Trifluoroacetic acid → HCID 131711825, compound

HRID 2057854Notes

Reaction equation

HRID 2057854 reaction equation
[NH:1](C(OC(C1C=C(OC)C=C(OC)C=1)(C)C)=O)[C@H:2]([C:24]([NH:26][C@H:27]([C:49]([NH:51][C@H:52]([C:60]([NH:62][C@H:63]([C:70]([NH:72][C@H:73]([C:78]([NH:80][C@H:81]([C:103]([NH:105][C@H:106]([C:109]([NH:111][C@H:112]([C:117]([NH:119][C@H:120]([C:133]([NH:135][C@H:136]([C:142]([NH:144][C@H:145]([C:150]([NH:152][C@H:153]([C:163]([NH:165][C@H:166]([C:171]([NH:173][C@H:174]([C:187]([NH:189][C@H:190]([C:212]([NH:214][C@H:215]([C:220]([O:222][C:223]([CH3:226])([CH3:225])[CH3:224])=[O:221])[CH2:216][C:217](=[O:219])[NH2:218])=[O:213])[CH2:191][S:192][C:193]([C:206]1[CH:211]=[CH:210][CH:209]=[CH:208][CH:207]=1)([C:200]1[CH:205]=[CH:204][CH:203]=[CH:202][CH:201]=1)[C:194]1[CH:199]=[CH:198][CH:197]=[CH:196][CH:195]=1)=[O:188])[CH2:175][C:176]1[CH:181]=[CH:180][C:179]([O:182][C:183]([CH3:186])([CH3:185])[CH3:184])=[CH:178][CH:177]=1)=[O:172])[CH2:167][C:168](=[O:170])[NH2:169])=[O:164])[CH2:154][CH2:155][C:156](=[O:162])[O:157][C:158]([CH3:161])([CH3:160])[CH3:159])=[O:151])[CH2:146][CH:147]([CH3:149])[CH3:148])=[O:143])[CH2:137][CH2:138][C:139](=[O:141])[NH2:140])=[O:134])[CH2:121][C:122]1[CH:127]=[CH:126][C:125]([O:128][C:129]([CH3:132])([CH3:131])[CH3:130])=[CH:124][CH:123]=1)=[O:118])[CH2:113][CH:114]([CH3:116])[CH3:115])=[O:110])[CH2:107][OH:108])=[O:104])[CH2:82][S:83][C:84]([C:97]1[CH:102]=[CH:101][CH:100]=[CH:99][CH:98]=1)([C:91]1[CH:96]=[CH:95][CH:94]=[CH:93][CH:92]=1)[C:85]1[CH:90]=[CH:89][CH:88]=[CH:87][CH:86]=1)=[O:79])[C@H:74]([CH2:76][CH3:77])[CH3:75])=[O:71])[CH2:64][O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:61])[C@@H:53]([CH3:59])[O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:50])[CH2:28][S:29][C:30]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:25])[CH2:3][S:4][C:5]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[F:243][C:244]([F:249])([F:248])[C:245]([OH:247])=[O:246].FC(F)(F)C(O)=O.C(Cl)Cl.C1(OC)C=CC=CC=1>N1C=CC=CC=1.O.C(Cl)Cl>[NH2:1][C@H:2]([C:24]([NH:26][C@H:27]([C:49]([NH:51][C@H:52]([C:60]([NH:62][C@H:63]([C:70]([NH:72][C@H:73]([C:78]([NH:80][C@H:81]([C:103]([NH:105][C@H:106]([C:109]([NH:111][C@H:112]([C:117]([NH:119][C@H:120]([C:133]([NH:135][C@H:136]([C:142]([NH:144][C@H:145]([C:150]([NH:152][C@H:153]([C:163]([NH:165][C@H:166]([C:171]([NH:173][C@H:174]([C:187]([NH:189][C@H:190]([C:212]([NH:214][C@H:215]([C:220]([O:222][C:223]([CH3:224])([CH3:225])[CH3:226])=[O:221])[CH2:216][C:217](=[O:219])[NH2:218])=[O:213])[CH2:191][S:192][C:193]([C:200]1[CH:201]=[CH:202][CH:203]=[CH:204][CH:205]=1)([C:194]1[CH:199]=[CH:198][CH:197]=[CH:196][CH:195]=1)[C:206]1[CH:207]=[CH:208][CH:209]=[CH:210][CH:211]=1)=[O:188])[CH2:175][C:176]1[CH:181]=[CH:180][C:179]([O:182][C:183]([CH3:185])([CH3:186])[CH3:184])=[CH:178][CH:177]=1)=[O:172])[CH2:167][C:168](=[O:170])[NH2:169])=[O:164])[CH2:154][CH2:155][C:156](=[O:162])[O:157][C:158]([CH3:161])([CH3:159])[CH3:160])=[O:151])[CH2:146][CH:147]([CH3:149])[CH3:148])=[O:143])[CH2:137][CH2:138][C:139](=[O:141])[NH2:140])=[O:134])[CH2:121][C:122]1[CH:123]=[CH:124][C:125]([O:128][C:129]([CH3:132])([CH3:131])[CH3:130])=[CH:126][CH:127]=1)=[O:118])[CH2:113][CH:114]([CH3:115])[CH3:116])=[O:110])[CH2:107][OH:108])=[O:104])[CH2:82][S:83][C:84]([C:85]1[CH:86]=[CH:87][CH:88]=[CH:89][CH:90]=1)([C:91]1[CH:96]=[CH:95][CH:94]=[CH:93][CH:92]=1)[C:97]1[CH:102]=[CH:101][CH:100]=[CH:99][CH:98]=1)=[O:79])[C@H:74]([CH2:76][CH3:77])[CH3:75])=[O:71])[CH2:64][O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:61])[C@@H:53]([CH3:59])[O:54][C:55]([CH3:56])([CH3:57])[CH3:58])=[O:50])[CH2:28][S:29][C:30]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)([C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:25])[CH2:3][S:4][C:5]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[F:243][C:244]([C:245]([OH:247])=[O:246])([F:249])[F:248]

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 21863450Trifluoroacetic acid methylene chlorideHCID 131711827HCID 131711827, compound

Product 1

HCID 131711825HCID 131711825, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

10.26 g (3 mmoles) of Ddz-Cys(Trt)-Cys(Trt)-Thr(But)-Ser(But)-Ile-Cys(Trt)-Ser-Leu-Tyr(But)-Gln-Leu-Glu(OBut)-Asn-Tyr(But)-Cys(Trt)-Asn-OBut are dissolved, while stirring, in a mixture of 5.25 ml (60 mmoles) of trifluoroacetic acid, 1.05 ml of water and 99 ml of methylene chloride (=about 105 ml of a 5 percent strength trifluoroacetic acid/methylene chloride solution containing 1% of water) and 10.5 ml of anisole. The mixture is stirred for 4 hours at room temperature. 10.5 ml of pyridine are then added and the mixture is concentrated. Remaining volatile material is distilled off in a high vacuum. The oily residue is triturated with ether and the precipitate is filtered off and dried. The substance is then washed with water and dried over P2O5. For further purification, the substance is boiled three times with 10 ml of ethyl acetate at a time and is in each case filtered off hot.

Workup

  1. concentrationthe mixture is concentrated
  2. distillationis distilled off in a high vacuum
  3. customThe oily residue is triturated with ether
  4. filtrationthe precipitate is filtered off
  5. customdried
  6. washThe substance is then washed with water
  7. dry with materialdried over P2O5
  8. customFor further purification
  9. filtrationfiltered off hot

Sources & evidence

ORD record
ord-a1133229340f4f6ea3f87541eea0d5f0
Source dataset
uspto-grants-1980_07
Patent number
US04212796

Reaction notes

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