Methanol → (2S,4R)-2-amino-5-[2-benzyloxymethyl-4-tritylsulfanyl-pyrrolidine-1-sulfonyl]-benzoic acid methyl ester
Reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]1[CH2:14][C@@H:13]([S:15][C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][N:11]1[S:35]([C:38]1[CH:49]=[CH:48][C:41]2[NH:42][C:43](=O)[O:44][C:45](=[O:46])[C:40]=2[CH:39]=1)(=[O:37])=[O:36])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[CH3:43][O:44][C:45](=[O:46])[C:40]1[CH:39]=[C:38]([S:35]([N:11]2[CH2:12][C@H:13]([S:15][C:16]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:14][C@H:10]2[CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)(=[O:37])=[O:36])[CH:49]=[CH:48][C:41]=1[NH2:42]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 0.72 g (1.05 mmol) (2S,4R)-6-(2-benzyloxymethyl-4-tritylsulfanyl-pyrrolidine-1-sulfonyl)-1H-benzo[d][1,3]oxazine-2,4-dione in 40 ml CH2Cl2 was treated at room temperature with 0.42 ml (10.5 mmol) MeOH and 0.31 ml (2.09 mmol) DBU and stirred for 6 h. Flash chromatography on silica gel (Hexane/EtOAc 9:1) gave (2S,4R)-2-amino-5-[2-benzyloxymethyl-4-tritylsulfanyl-pyrrolidine-1-sulfonyl]-benzoic acid methyl ester which was deprotected (following Method 3) to give (2S,4R)-2-amino-5-[2-benzyloxymethyl-4-mercapto-pyrrolidine-1-sulfonyl]-benzoic acid methyl ester, MS: 437 (M+H+).
Sources & evidence
- ORD record
- ord-5892e4e169264d738193c8e9d6986373
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07189756B2
Reaction notes
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