Trifluoroacetic acid → HCID 59001103, compound

HRID 507308Notes

Reaction equation

HRID 507308 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]([C@@H:26]([C:31](=[O:33])[NH2:32])[CH2:27][CH:28]([CH3:30])[CH3:29])[S:16]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([S:16]([N:15]([C@H:26]([CH2:27][CH:28]([CH3:30])[CH3:29])[C:31]([NH2:32])=[O:33])[CH2:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)(=[O:17])=[O:18])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 590010954-{[N-((1R)-1-Carbamoyl-3-methyl-butyl)-N-(4-chlorobenzenesulfonyl)amino]-methyl}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59001103HCID 59001103, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{[N-((1R)-1-carbamoyl-3-methyl-butyl)-N-(4-chlorobenzenesulfonyl)amino]-methyl}-piperidine-1-carboxylic acid tert-butyl ester (Example 92, 2.6 grams, 5.2 mmol) in CH2Cl2 (25 mL) was added trifluoroacetic acid (10 mL). The reaction was stirred at rt for 1 h and then was concentrated to give a white solid (1.6 grams, 84%). MS (ESI), (M+H)+ 402.15; 1H NMR (DMSO-d6, 500 MHz), δ 7-87 (d, 2H, J=8.5), 7.66 (d, 2H, J=8.6), 7.41 (s, 1H), 7.04 (s, 1H), 4.17 (t, 1H, J=7.3), 3.40-3.50 (m, 1H), 3.20-3.25 (m, 1H), 3.03-3.10 (m, 1H), 2.65-2.80 (m, 2H), 1.85-2.00 (m, 1H), 1.20-1.85 (m, 2H), 1.45-1.60 (m, 1H), 1.30-1.40 (m, 1H), 1.10-1.30 (m, 4H), 0.75-0.90 (m, 1H), 0.82 (d, 3H, J=7.3), 0.80 (d, 3H, J=7.0).

Workup

  1. concentrationwas concentrated

Sources & evidence

ORD record
ord-6e03558616ed4e69bbac0b81b50fee9b
Source dataset
uspto-grants-2010_08
Patent number
US07786122B2

Reaction notes

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