Trifluoroacetic acid → HCID 86607894, compound

HRID 736793Notes

Reaction equation

HRID 736793 reaction equation
[C:1]([O:5][NH:6][C:7]([C@:9]1([OH:45])[C@H:14]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=[C:29]([CH3:37])[CH:28]=3)=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]1)=[O:8])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O>C(Cl)Cl>[C:1]([O:5][NH:6][C:7]([C@:9]1([OH:45])[C@H:14]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=[C:29]([CH3:37])[CH:28]=3)=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:13][CH2:12][NH:11][CH2:10]1)=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86607893HCID 86607893, compound

Product 1

HCID 86607894HCID 86607894, compoundYield 137.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (3R,4R)-3-[(tert-butoxyamino)carbonyl]-3-hydroxy-4-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]piperidine-1-carboxylate (740 mg, 1.15 mmol) in CH2Cl2 (10 mL) was added trifluoroacetic acid (2.5 mL). The reaction was stirred at room temperature for 1.5 h. The solvent was concentrated in vacuo and methanol was used to chase residual trifluoroacetic acid. The residue was precipitated from ether as a white solid to yield 856 mg (97%) of (3R,4R)-N-tert-butoxy-3-hydroxy-4-(4-((2-methylquinolin-4-yl) methoxy)phenylsulfonamido)piperidine-3-carboxamide as the trifluoroacetic acid salt. MS: (M+H)+=543.1.

Workup

  1. concentrationThe solvent was concentrated in vacuo and methanol
  2. customThe residue was precipitated from ether as a white solid

Sources & evidence

ORD record
ord-e097bfa873ba49b587df60d98d986770
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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