Trifluoroacetic acid → 3(R)-[3-(biphenyl-4-yl)-1H-pyrrol-1-yl]-N-[2,2-dimethyl-1(S)-(methylcarbamoyl)propyl]succinamic acid benzyl ester

HRID 382136Notes

Reaction equation

HRID 382136 reaction equation
[CH2:1]([O:8][C:9](=[O:25])[CH2:10][C@@H:11]([NH2:24])[C:12]([NH:14][C@H:15]([C:20](=[O:23])[NH:21][CH3:22])[C:16]([CH3:19])([CH3:18])[CH3:17])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]1([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:31]=[CH:30][C:29]([CH:32]2[CH2:36][CH:35](OC)O[CH:33]2OC)=[CH:28][CH:27]=1.FC(F)(F)C(O)=O>ClCCCl>[CH2:1]([O:8][C:9](=[O:25])[CH2:10][C@@H:11]([N:24]1[CH:35]=[CH:36][C:32]([C:29]2[CH:30]=[CH:31][C:26]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[CH:27][CH:28]=2)=[CH:33]1)[C:12]([NH:14][C@H:15]([C:20](=[O:23])[NH:21][CH3:22])[C:16]([CH3:18])([CH3:19])[CH3:17])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 183803263-Biphenyl-4-yl-2,5-dimethoxytetrahydrofuranHCID 545497963(R)-amino-N-(2,2-dimethyl-1(S)-(methylcarbamoyl)propyl)succinamic acid benzyl ester

Product 1

HCID 599245053(R)-[3-(biphenyl-4-yl)-1H-pyrrol-1-yl]-N-[2,2-dimethyl-1(S)-(methylcarbamoyl)propyl]succinamic acid benzyl esterYield 35%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

According to the procedure described in Example 1(c) for the preparation of N-(8-oxo-4oxa-1,7-diaza-tricyclo-[9.6.1.012,17]-octa-deca-11(18),12,14,16-tetraen-9S-yl)-3(R)-(3-phenyl-1H-pyrrol-1-yl)succinamic acid benzyl ester, 3(R)-amino-N-(2,2-dimethyl-1(S)-(methylcarbamoyl)propyl)succinamic acid benzyl ester (prepared as described in Example 1(b))was condensed with 3-biphenyl-4-yl-2,5-dimethoxy-tetrahydrofuran (prepared as described in Example 1(a)) in 1,2-dichloroethane with trifluoroacetic acid to provide in 35% yield 3(R)-[3-(biphenyl-4-yl)-1H-pyrrol-1-yl]-N-[2,2-dimethyl-1(S)-(methylcarbamoyl)propyl]succinamic acid benzyl ester as an amorphous solid.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-83485fa048464eaea71ff72c2cb4072e
Source dataset
uspto-grants-2001_10
Patent number
US06306892B1

Reaction notes

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