Hydrochloric Acid → Butyric acid (2R,5R)-5-[(1S,2S)-2-acetylamino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-morpholin-2-ylmethyl ester hydrochloride

HRID 20477Notes

Reaction equation

HRID 20477 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]([CH2:30][O:31][C:32](=[O:36])[CH2:33][CH2:34][CH3:35])[CH2:9]1)=O)(C)(C)C.[ClH:37].O1CCOCC1>>[ClH:37].[C:26]([NH:25][C@@H:15]([CH2:16][C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[CH:18]=1)[C@@H:14]([C@@H:13]1[NH:8][CH2:9][C@H:10]([CH2:30][O:31][C:32](=[O:36])[CH2:33][CH2:34][CH3:35])[O:11][CH2:12]1)[OH:29])(=[O:28])[CH3:27]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 68563008(R)-5-[(1S,2S)-2-acetylamino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2-butyryloxymethyl-morpholine-4-carboxylic acid tert-butyl ester

Product 1

HCID 86615367Butyric acid (2R,5R)-5-[(1S,2S)-2-acetylamino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-morpholin-2-ylmethyl ester hydrochlorideYield 100%

Procedure

To (R)-5-[(1S,2S)-2-acetylamino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2-butyryloxymethyl-morpholine-4-carboxylic acid tert-butyl ester (0.022 g, 0.043 mmol) add 4 M hydrogen chloride in 1,4-dioxane (0.500 mL, 2.00 mmol) and stir for 45 minutes. Concentrate under reduced pressure to give the title compound as an off-white solid (20.0 mg, 100%).

Workup

  1. concentrationConcentrate under reduced pressure

Sources & evidence

ORD record
ord-ca97306d46fa47ff9d2685213146a619
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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