Acetic Anhydride → [(5R)-3-(3-fluorophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl acetate

HRID 1782080Notes

Reaction equation

HRID 1782080 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][C@H:11]([CH2:13][OH:14])[O:10][C:9]2=[O:15])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:23](OC(=O)C)(=[O:25])[CH3:24].C(=O)(O)[O-].[Na+]>ClCCl.CN(C)C1C=CN=CC=1>[F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][C@H:11]([CH2:13][O:14][C:23](=[O:25])[CH3:24])[O:10][C:9]2=[O:15])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 11229590(R)-3-(3-Fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one

Product 1

HCID 20788912[(5R)-3-(3-fluorophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl acetateYield 103.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

(5R)-3-(3-Fluorophenyl)-5-hydroxymethyl-1,3-oxazolidin-2-one (40 g, 0.189 M, see Upjohn WO 94-13649) was suspended by stirring in dry dichloromethane (400 mL) under nitrogen. Triethylamine (21 g, 0.208 M) and 4-dimethylaminopyridine (0.6 g, 4.9 mM) were added, followed by dropwise addition of acetic anhydride (20.3 g, 0.199 M) over 30 minutes, and stirring continued at ambient temperature for 18 hours. Saturated aqueous sodium bicarbonate (250 mL) was added, the organic phase separated, washed with 2% sodium dihydrogen phosphate, dried (magnesium sulfate), filtered and evaporated to give the desired product (49.6 g) as an oil.

Workup

  1. customthe organic phase separated
  2. washwashed with 2% sodium dihydrogen phosphate
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-66c741410bb345ed9d80b0aae8b6e2b4
Source dataset
uspto-grants-2009_03
Patent number
US07498350B2

Reaction notes

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