1-[[2-Chloro-4-(tributylstannyl)benzoyl]oxy]-2,5-pyrrolidinedione → N-[2-chloro-4-(tri-n-butylstannyl)benzoyl]-3-(thiophene-2-carbonyl)amino-L-alanine

HRID 393109Notes

Reaction equation

HRID 393109 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][CH2:9][C@@H:10]([C:12]([OH:14])=[O:13])[NH2:11])=[O:7].[Cl:15][C:16]1[CH:31]=[C:30]([Sn:32]([CH2:41][CH2:42][CH2:43][CH3:44])([CH2:37][CH2:38][CH2:39][CH3:40])[CH2:33][CH2:34][CH2:35][CH3:36])[CH:29]=[CH:28][C:17]=1[C:18](ON1C(=O)CCC1=O)=[O:19]>CN(C)C=O>[Cl:15][C:16]1[CH:31]=[C:30]([Sn:32]([CH2:37][CH2:38][CH2:39][CH3:40])([CH2:41][CH2:42][CH2:43][CH3:44])[CH2:33][CH2:34][CH2:35][CH3:36])[CH:29]=[CH:28][C:17]=1[C:18]([NH:11][C@H:10]([C:12]([OH:14])=[O:13])[CH2:9][NH:8][C:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)=[O:7])=[O:19]

Participants

4

Reactant 2

HCID 159086841-[[2-Chloro-4-(tributylstannyl)benzoyl]oxy]-2,5-pyrrolidinedioneHCID 688202073-(thiophene-2-carbonyl)amino-L-alanine

Product 1

HCID 68819630N-[2-chloro-4-(tri-n-butylstannyl)benzoyl]-3-(thiophene-2-carbonyl)amino-L-alanine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(thiophene-2-carbonyl)amino-L-alanine on Wang resin (2.00 g) and 1-[[2-chloro-4-(tributylstannyl)benzoyl]oxy]-2,5-pyrrolidinedione (Example 374; 2.50 g, 4.6 mmol) in N,N-dimethylformamide was shaken for 72 h. The resin was washed with dichloromethane and methanol to give N-[2-chloro-4-(tri-n-butylstannyl)benzoyl]-3-(thiophene-2-carbonyl)amino-L-alanine on Wang resin.

Workup

  1. washThe resin was washed with dichloromethane and methanol

Sources & evidence

ORD record
ord-853d7be51abb47dbaf62a2f330b643a3
Source dataset
uspto-grants-2004_10
Patent number
US06803384B2

Reaction notes

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