Water → HCID 131711811, compound

HRID 2057847Notes

Reaction equation

HRID 2057847 reaction equation
[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(C)(C)C)=[O:150])[CH2:145][C:146](=[O:148])[NH2:147])=[O:142])[CH2:120][S:121]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:117])[CH2:104][C:105]1[CH:110]=[CH:109][C:108]([O:111]C(C)(C)C)=[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(C)(C)C)=[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(C)(C)C)=[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(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4].FC(C(O)=O)(F)F.O>C(S)C.FC(F)(F)C(O)=O>[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]([OH:151])=[O:150])[CH2:145][C:146](=[O:148])[NH2:147])=[O:142])[CH2:120][SH:121])=[O:117])[CH2:104][C:105]1[CH:106]=[CH:107][C:108]([OH:111])=[CH:109][CH:110]=1)=[O:101])[CH2:96][C:97](=[O:99])[NH2:98])=[O:93])[CH2:83][CH2:84][C:85](=[O:86])[OH:91])=[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:52]=[CH:53][C:54]([OH:57])=[CH:55][CH:56]=1)=[O:47])[CH2:42][CH:43]([CH3:44])[CH3:45])=[O:39])[CH2:36][OH:37])=[O:33])[CH2:11][SH:12])=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4]

Participants

5

Reactant 2

HCID 962WaterHCID 131711812HCID 131711812, compound

Product 1

HCID 131711811HCID 131711811, compound

Reagents, catalysts & solvents 2

HCID 6343EthanethiolSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

3.429 g (1.5 mmoles) of H-Ile-Cys(Trt)-Ser-Leu-Tyr(But)-Gln-Leu-Glu(OBut)-Asn-Tyr(But)-Cys(Trt)-Asn-OBut trifluoroacetate are dissolved in a mixture of 19 ml of ethylmercaptan and 19 ml of trifluoroacetic acid. The reaction mixture is stirred for 4 hours at room temperature and is then poured into 250 ml of water, while stirring. The precipitate is filtered off, washed with ether and dried. It is then triturated with ether, filtered off and dried. Yield 1.964 g. This substance is then deblocked once more as described above. Yield 1.6 g (61%). In total, a further 330 mg of substance was obtainable from the filtrates after extraction with ether and freeze-drying.

Workup

  1. stirringwhile stirring
  2. filtrationThe precipitate is filtered off
  3. washwashed with ether
  4. customdried
  5. customIt is then triturated with ether
  6. filtrationfiltered off
  7. customdried
  8. extractionafter extraction with ether
  9. customfreeze-drying

Sources & evidence

ORD record
ord-1fd3d15dcf3d433f8e294b626af86d81
Source dataset
uspto-grants-1980_07
Patent number
US04212796

Reaction notes

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