Trifluoroacetic acid → N-[(1S,2S)-1-(3,5-Difluorobenzyl)-2-((3R,6S)-6-ethoxymorpholin-3-yl)-2-hydroxyethyl]-acetamide trifluoroacetate

HRID 20475Notes

Reaction equation

HRID 20475 reaction equation
C(OC([N:8]1[CH:13]([C@@H:14]([OH:29])[C@@H:15]([NH:25][C:26](=[O:28])[CH3:27])[CH2:16][C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[CH:18]=2)[CH2:12][O:11][C@@H:10]([O:30][CH2:31][CH3:32])[CH2:9]1)=O)(C)(C)C.[F:33][C:34]([F:39])([F:38])[C:35]([OH:37])=[O:36]>ClCCl>[F:33][C:34]([F:39])([F:38])[C:35]([OH:37])=[O:36].[F:24][C:19]1[CH:18]=[C:17]([CH:22]=[C:21]([F:23])[CH:20]=1)[CH2:16][C@H:15]([NH:25][C:26](=[O:28])[CH3:27])[C@@H:14]([C@H:13]1[CH2:12][O:11][C@H:10]([O:30][CH2:31][CH3:32])[CH2:9][NH:8]1)[OH:29]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68558820(R)-5-[(1S,2S)-2-Acetylamino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2-ethoxymorpholine-4-carboxylic acid tert-butyl ester

Product 1

HCID 68562026N-[(1S,2S)-1-(3,5-Difluorobenzyl)-2-((3R,6S)-6-ethoxymorpholin-3-yl)-2-hydroxyethyl]-acetamide trifluoroacetateYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve (R)-5-[(1S,2S)-2-acetylamino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2-ethoxymorpholine-4-carboxylic acid tert-butyl ester (0.060 g, 0.131 mmol) in dichloromethane (5 mL) and add trifluoroacetic acid (0.74 g, 6.5 mmol). Stir at room temperature for 1.5 hours and concentrate to give the title compound (60 mg, 97%).

Workup

  1. concentrationconcentrate

Sources & evidence

ORD record
ord-e5e384c1dfb1450e955e3e7c97087d8b
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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