Pyridine → HCID 131711838, compound

HRID 2058403Notes

Reaction equation

HRID 2058403 reaction equation
[NH:1](C(OC(C1C=C(OC)C=C(OC)C=1)(C)C)=O)[C@H:2]([C:7]([NH:9][C@H:10]([C:32]([NH:34][C@H:35]([C:38]([NH:40][C@H:41]([C:46]([NH:48][C@H:49]([C:62]([NH:64][C@H:65]([C:71]([NH:73][C@H:74]([C:79]([NH:81][C@H:82]([C:92]([NH:94][C@H:95]([C:100]([NH:102][C@H:103]([C:116]([NH:118][C@H:119]([C:141]([NH:143][C@H:144]([C:149]([O:151][C:152]([CH3:155])([CH3:154])[CH3:153])=[O:150])[CH2:145][C:146](=[O:148])[NH2:147])=[O:142])[CH2:120][S:121][C:122]([C:135]1[CH:140]=[CH:139][CH:138]=[CH:137][CH:136]=1)([C:129]1[CH:134]=[CH:133][CH:132]=[CH:131][CH:130]=1)[C:123]1[CH:128]=[CH:127][CH:126]=[CH:125][CH:124]=1)=[O:117])[CH2:104][C:105]1[CH:110]=[CH:109][C:108]([O:111][C:112]([CH3:115])([CH3:114])[CH3:113])=[CH:107][CH:106]=1)=[O:101])[CH2:96][C:97](=[O:99])[NH2:98])=[O:93])[CH2:83][CH2:84][C:85](=[O:91])[O:86][C:87]([CH3:90])([CH3:89])[CH3:88])=[O:80])[CH2:75][CH:76]([CH3:78])[CH3:77])=[O:72])[CH2:66][CH2:67][C:68](=[O:70])[NH2:69])=[O:63])[CH2:50][C:51]1[CH:56]=[CH:55][C:54]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[CH:53][CH:52]=1)=[O:47])[CH2:42][CH:43]([CH3:45])[CH3:44])=[O:39])[CH2:36][OH:37])=[O:33])[CH2:11][S:12][C:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4].[F:172][C:173]([F:178])([F:177])[C:174]([OH:176])=[O:175].N1C=CC=CC=1>O.C(Cl)Cl.FC(F)(F)C(O)=O.C(Cl)Cl.C1(OC)C=CC=CC=1>[NH2:1][C@H:2]([C:7]([NH:9][C@H:10]([C:32]([NH:34][C@H:35]([C:38]([NH:40][C@H:41]([C:46]([NH:48][C@H:49]([C:62]([NH:64][C@H:65]([C:71]([NH:73][C@H:74]([C:79]([NH:81][C@H:82]([C:92]([NH:94][C@H:95]([C:100]([NH:102][C@H:103]([C:116]([NH:118][C@H:119]([C:141]([NH:143][C@H:144]([C:149]([O:151][C:152]([CH3:153])([CH3:154])[CH3:155])=[O:150])[CH2:145][C:146](=[O:148])[NH2:147])=[O:142])[CH2:120][S:121][C:122]([C:123]1[CH:124]=[CH:125][CH:126]=[CH:127][CH:128]=1)([C:135]1[CH:140]=[CH:139][CH:138]=[CH:137][CH:136]=1)[C:129]1[CH:130]=[CH:131][CH:132]=[CH:133][CH:134]=1)=[O:117])[CH2:104][C:105]1[CH:110]=[CH:109][C:108]([O:111][C:112]([CH3:114])([CH3:115])[CH3:113])=[CH:107][CH:106]=1)=[O:101])[CH2:96][C:97](=[O:99])[NH2:98])=[O:93])[CH2:83][CH2:84][C:85](=[O:91])[O:86][C:87]([CH3:88])([CH3:90])[CH3:89])=[O:80])[CH2:75][CH:76]([CH3:77])[CH3:78])=[O:72])[CH2:66][CH2:67][C:68](=[O:70])[NH2:69])=[O:63])[CH2:50][C:51]1[CH:56]=[CH:55][C:54]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[CH:53][CH:52]=1)=[O:47])[CH2:42][CH:43]([CH3:44])[CH3:45])=[O:39])[CH2:36][OH:37])=[O:33])[CH2:11][S:12][C:13]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4].[F:172][C:173]([F:178])([F:177])[C:174]([O-:176])=[O:175]

Participants

8

Reactant 3

HCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 131711814HCID 131711814, compound

Product 1

HCID 131711838HCID 131711838, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 7519AnisoleSolventHCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

24 g (about 10 mmols) of Ddz-Ile-Cys(Trt)-Ser-Leu-Tyr(But)-Gln-Leu-Glu(OBut)-Asn-Tyr(But)-Cys(Trt)-Asn-OBut were dissolved in a mixture of 8.75 ml (100 mmols) trifluoroacetic acid, 1.75 ml of water, 165 ml of methylene chloride (=about 175 ml of a 5% strength trifluoroacetic acid-methylene chloride solution with 1% of water) and 17.5 ml anisole while stirring. Stirring was continued for 4 hours at room temperature, 10 ml (124 mmols) pyridine were then added and the mixture was concentrated. The residue was triturated with ether, filtered of with suction, washed with ether and dried in vacuo. Next, the substance was triturated with water, filtered off with suction, washed with water and dried over P2O5.

Workup

  1. stirringStirring
  2. concentrationthe mixture was concentrated
  3. customThe residue was triturated with ether
  4. filtrationfiltered of with suction
  5. washwashed with ether
  6. customdried in vacuo
  7. customNext, the substance was triturated with water
  8. filtrationfiltered off with suction
  9. washwashed with water
  10. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-7e6b1280659742c3b8c8a8b9e968cb2b
Source dataset
uspto-grants-1980_07
Patent number
US04215037

Reaction notes

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