Phenethylamine → (2S,4R)-4-(4-Methoxy-benzylsulfanyl)-1-(2-phenyl-ethanesulfonyl)-pyrrolidine-2-carboxylic acid benzyl-methyl-amide

HRID 1264405Notes

Reaction equation

HRID 1264405 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][S:8][C@H:9]2[CH2:13][N:12]([S:14]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)(=[O:16])=[O:15])[C@H:11]([C:25]([OH:27])=O)[CH2:10]2)=[CH:5][CH:4]=1.[CH2:30](CN)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C[CH2:40][N:41]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.OS([O-])(=O)=O.[K+].CCOC(C)=O>C1COCC1>[CH2:30]([N:41]([CH3:40])[C:25]([C@@H:11]1[CH2:10][C@@H:9]([S:8][CH2:7][C:6]2[CH:28]=[CH:29][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:13][N:12]1[S:14]([CH2:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)(=[O:15])=[O:16])=[O:27])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

7

Reactant 5

HCID 1001PhenethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 70002412(2S,4R)-4-(4-Methoxy-benzylsulfanyl)-1-(2-phenyl-ethanesulfonyl)-pyrrolidine-2-carboxylic acidHCID 86585043ethylacetate KHSO4

Product 1

HCID 70001990(2S,4R)-4-(4-Methoxy-benzylsulfanyl)-1-(2-phenyl-ethanesulfonyl)-pyrrolidine-2-carboxylic acid benzyl-methyl-amideYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 242 mg (0.4 mmol) (2S,4R)-4-(4-Methoxy-benzylsulfanyl)-1-(2-phenyl-ethanesulfonyl)-pyrrolidine-2-carboxylic acid in 4 ml THF was treated at 0° C. with 0.057 ml (0.44 mmol) N-benzylmethylamine, 92 mg (0.48 mmol) EDCI , 6.1 mg (0.04 mmol) HOBT and warmed up over night to RT. The reaction was poured into aqueous 10% KHSO4/EtOAc (3×). The organic phases were washed with aqueous 10% NaCl solution and dried over Na2SO4 to give after flash silicagel column (Hexane/EtOAc 4:1) 21 mg (10%) (2S,4R)-4-(4-Methoxy-benzylsulfanyl)-1-(2-phenyl-ethanesulfonyl)-pyrrolidine-2-carboxylic acid benzyl-methyl-amide, MS: 539 (MH+).

Workup

  1. washThe organic phases were washed with aqueous 10% NaCl solution
  2. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-5af1271228e54640b02c9ecc19693e82
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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