Methyl (2R)-2-amino-3-[(acetamidomethyl)sulfanyl]propanoate → Trt-Cys(Trt)-Cys(Acm)-OMe

HRID 1731229Notes

Reaction equation

HRID 1731229 reaction equation
[NH:1]([C:34]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C@H:2]([C:24](ON1C(=O)CCC1=O)=[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.[NH2:53][C@H:54]([C:62]([O:64][CH3:65])=[O:63])[CH2:55][S:56][CH2:57][NH:58][C:59]([CH3:61])=[O:60]>C(Cl)(Cl)Cl>[NH:1]([C:34]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[C@H:2]([C:24]([NH:53][C@H:54]([C:62]([O:64][CH3:65])=[O:63])[CH2:55][S:56][CH2:57][NH:58][C:59]([CH3:61])=[O:60])=[O:25])[CH2:3][S:4][C:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 14991594Methyl (2R)-2-amino-3-[(acetamidomethyl)sulfanyl]propanoateHCID 88804794Trt-Cys(Trt)-OSu

Product 1

HCID 131710552Trt-Cys(Trt)-Cys(Acm)-OMe

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

7.0 g of Trt-Cys(Trt)-OSu and 2.0 g of H-Cys(Acm)-OMe in 50 ml of chloroform are left to stand for 20 hours at room temperature. The solution is then diluted with 100 ml of chloroform and washed with 1 N citric acid, 1 N sodium bicarbonate and water, dried over sodium sulphate and evaporated. The residue is recrystallised from ethyl acetate-ether. Melting point 197°-198°C.

Workup

  1. washwashed with 1 N citric acid, 1 N sodium bicarbonate and water
  2. dry with materialdried over sodium sulphate
  3. customevaporated
  4. customThe residue is recrystallised from ethyl acetate-ether

Sources & evidence

ORD record
ord-63edf12cdeb245f9a098ec0ef469e8fa
Source dataset
uspto-grants-1976_11
Patent number
US03994871

Reaction notes

Loading…