Dicyclohexylcarbodiimide → Trt-Cys(Trt)-Cys(Acm)-Thr(But)-Ser(But)-OMe

HRID 1731233Notes

Reaction equation

HRID 1731233 reaction equation
[NH:1]([C:38]([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C@H:2]([C:24]([NH:26][C@H:27]([C:35](O)=[O:36])[CH2:28][S:29][CH2:30][NH:31][C:32]([CH3:34])=[O:33])=[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.[NH2:57][C@H:58]([C:66]([NH:68][C@H:69]([C:76]([O:78][CH3:79])=[O:77])[CH2:70][O:71][C:72]([CH3:75])([CH3:74])[CH3:73])=[O:67])[C@@H:59]([CH3:65])[O:60][C:61]([CH3:64])([CH3:63])[CH3:62].C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1>C(OCC)(=O)C>[NH:1]([C:38]([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)([C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C@H:2]([C:24]([NH:26][C@H:27]([C:35]([NH:57][C@H:58]([C:66]([NH:68][C@H:69]([C:76]([O:78][CH3:79])=[O:77])[CH2:70][O:71][C:72]([CH3:75])([CH3:74])[CH3:73])=[O:67])[C@@H:59]([CH3:65])[O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:36])[CH2:28][S:29][CH2:30][NH:31][C:32]([CH3:34])=[O:33])=[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:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 131710553Trt-Cys(Trt)-Cys(Acm)-OHHCID 131710555H-Thr(But)-Ser(But)-OMe

Product 1

HCID 131710556Trt-Cys(Trt)-Cys(Acm)-Thr(But)-Ser(But)-OMe

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5.43 g of Trt-Cys(Trt)-Cys(Acm)-OH and 2.33 g of H-Thr(But)-Ser(But)-OMe are dissolved in 70 ml of ethyl acetate and 1.55 g of dicyclohexylcarbodiimide and 1.02 g of N-hydroxybenzotriazole are added at 0°C. After 4 hours at 0°C and 17 hours at 4°C, the mixture is filtered and the solution is diluted with 200 ml of ethyl acetate and washed with 1 N citric acid, 1 N sodium bicarbonate and water. After drying over sodium sulphate, the solution is evaporated and the residue is reprecipitated from ether acetatepetroleum ether.

Workup

  1. filtration17 hours at 4°C, the mixture is filtered
  2. additionthe solution is diluted with 200 ml of ethyl acetate
  3. washwashed with 1 N citric acid, 1 N sodium bicarbonate and water
  4. dry with materialAfter drying over sodium sulphate
  5. customthe solution is evaporated
  6. customthe residue is reprecipitated from ether acetatepetroleum ether

Sources & evidence

ORD record
ord-94ccc216688c47658a13901343b3bea6
Source dataset
uspto-grants-1976_11
Patent number
US03994871

Reaction notes

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