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

HRID 20476Notes

Reaction equation

C(OC([N:8]1[C@@H: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][CH2:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:9]1)=O)(C)(C)C.[F:37][C:38]([F:43])([F:42])[C:39]([OH:41])=[O:40]>>[F:37][C:38]([F:43])([F:42])[C:39]([OH:41])=[O:40].[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][CH2:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:9][NH:8]1)[OH:29]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 68559571(2R,5R)-5-[(1S,2S)-2-Acetylamino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2-(3,3-dimethylbutoxy)-morpholine-4-carboxylic acid tert-butyl ester

Product 1

HCID 68562971N-{(1S,2S)-1-(3,5-Difluorobenzyl)-2-[(3R,6R)-6-(3,3-dimethylbutoxy)-morpholin-3-yl]-2-hydroxyethyl}-acetamide trifluoroacetateYield 98.8%

Procedure

Dissolve (2R,5R)-5-[(1S,2S)-2-acetylamino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2-(3,3-dimethylbutoxy)-morpholine-4-carboxylic acid tert-butyl ester (0.14 g, 0.27 mmol) in trifluoroacetic acid (2 mL) and stir 10 minutes. Concentrate to give the title compound. (0.14 g, 98.8% yield).

Workup

concentrationConcentrate

Sources & evidence

ORD record: ord-5f48760a722647089781555b9e96f770
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745438B2

Reaction notes

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