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Acetic Anhydride → (R)-4-[(1S,2S)-2-Acetylamino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

HRID 20334
Notes
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Reaction equation

HRID 20334 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C@@H:13]([OH:25])[C@@H:14]([NH2:24])[CH2:15][C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[C:18]([F:23])[CH:17]=2)[CH2:11][O:10][C:9]1([CH3:27])[CH3:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:35](OC(=O)C)(=[O:37])[CH3:36]>O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C@@H:13]([OH:25])[C@@H:14]([NH:24][C:35](=[O:37])[CH3:36])[CH2:15][C:16]2[CH:17]=[C:18]([F:23])[CH:19]=[C:20]([F:22])[CH:21]=2)[CH2:11][O:10][C:9]1([CH3:27])[CH3:26])=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 68562294(R)-4-[(1S,2S)-2-Amino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

Product 1

HCID 68562048(R)-4-[(1S,2S)-2-Acetylamino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl esterYield 72.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

Dissolve (R)-4-[(1S,2S)-2-amino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (920 mg, 2.38 mmol) in dry tetrahydrofuran (20 ml) under an atmosphere of nitrogen. Add to the resulting solution triethylamine (400 μl, 2.87 mmol) and acetic anhydride (235 μL, 2.49 mmol). After 1 hour, dilute with ethyl acetate and wash with water (twice), 0.1 N hydrochloric acid, and saturated aqueous sodium chloride. Dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography 0:100 to 70:30 ethyl acetate:hexanes) to give the desired compound as a white solid (738 mg, 72% yield).

Workup

  1. washwash with water (twice), 0.1 N hydrochloric acid, and saturated aqueous sodium chloride
  2. dry with materialDry (magnesium sulfate)
  3. filtrationfilter
  4. concentrationconcentrate
  5. custompurify (silica gel chromatography 0:100 to 70:30 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-b8a6b8a65b8747e98b6747c02dd6c0f8
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07745438B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes