Trifluoroacetic acid methylene chloride → HCID 18337561, compound

HRID 1760804Notes

Reaction equation

HRID 1760804 reaction equation
C([O:5][C:6](=[O:33])[C@H:7]([N:11]([CH2:23][C:24]1[CH:32]=[CH:31][C:27]2[N:28]=[CH:29][NH:30][C:26]=2[CH:25]=1)[S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:8]([CH3:10])[CH3:9])(C)(C)C.FC(F)(F)C(O)=O.C(Cl)Cl>>[N:28]1[C:27]2[CH:31]=[CH:32][C:24]([CH2:23][N:11]([S:12]([C:15]3[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=3)(=[O:14])=[O:13])[C@H:7]([CH:8]([CH3:10])[CH3:9])[C:6]([OH:33])=[O:5])=[CH:25][C:26]=2[NH:30][CH:29]=1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 69762977HCID 69762977, compound

Product 1

HCID 18337561HCID 18337561, compoundYield 86.5%

Procedure

A solution of 2(R)-[(benzimidazol-5-ylmethyl)-(4-methoxybenzenesulfonyl)amino]-3-methylbutyric acid tert-butyl ester (74 mg, 0.156 mmol) in a 1:4 trifluoroacetic acid/methylene chloride mixture (5 mL) was stirred for 2 h. The reaction mixture was concentrated on a roto-evaporator and then on high-vac pump to give 2(R)-[(benzimidazol-5-ylmethyl)-(4-methoxy-benzenesulfonyl)amino]-3-methylbutyric acid (approx. 0.135 mmol).

Workup

  1. concentrationThe reaction mixture was concentrated on a roto-evaporator

Sources & evidence

ORD record
ord-1cabe4e6fdb44bd9a1221a881a3eb387
Source dataset
uspto-grants-2005_01
Patent number
US06844366B2

Reaction notes

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