Pyridine → HCID 131711812, compound

HRID 2057849Notes

Reaction equation

HRID 2057849 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].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: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]([C:174]([OH:176])=[O:175])([F:178])[F:177]

Participants

8

Reactant 5

HCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 21863450Trifluoroacetic acid methylene chlorideHCID 131711814HCID 131711814, compound

Product 1

HCID 131711812HCID 131711812, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

24 g (about 30 mmoles) of Ddz-Ile-Cys(Trt)-Ser-Leu-Tyr(But)-Gln-Leu-Glu(But)-Asn-Tyr(But)-Cys(Trt)-Asn-OBut are dissolved, whilst stirring, in a mixture of 8.75 ml (100 mmoles) of trifluoroacetic acid, 1.75 ml of water and 165 ml of methylene chloride (=about 175 ml of a 5% strength trifluoroacetic acid/methylene chloride solution containing 1% of water) and 17.5 ml of anisole. The mixture is stirred for 4 hours at room temperature. 10 ml (124 mmoles) of pyridine are then added and the mixture is concentrated. The residue is triturated with ether, filtered off, washed with ether and dried in vacuo. The substance is then triturated with water, filtered off, washed with water and dried over P2O5.

Workup

  1. concentrationthe mixture is concentrated
  2. customThe residue is triturated with ether
  3. filtrationfiltered off
  4. washwashed with ether
  5. customdried in vacuo
  6. customThe substance is then triturated with water
  7. filtrationfiltered off
  8. washwashed with water
  9. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-a6082a731fe84bbeb0e386e92127fd27
Source dataset
uspto-grants-1980_07
Patent number
US04212796

Reaction notes

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