Acetic Anhydride → HCID 57260073, compound

HRID 1167481Notes

Reaction equation

HRID 1167481 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][O:20][C:21]4[CH:25]=[CH:24][O:23][N:22]=4)[O:16][C:15]3=[O:26])=[CH:10][C:9]=2[F:27])[CH2:4]1.C(=O)(O)[O-].[Na+].[C:33](OC(=O)C)(=[O:35])[CH3:34]>ClCCl>[C:33]([NH:2][C@H:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][O:20][C:21]4[CH:25]=[CH:24][O:23][N:22]=4)[O:16][C:15]3=[O:26])=[CH:10][C:9]=2[F:27])[CH2:4]1)(=[O:35])[CH3:34]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 69981542HCID 69981542, compound

Product 1

HCID 57260073HCID 57260073, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-(4-((3S)-3-Amino-1-pyrrolidinyl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)-oxazolidin-2-one hydrochloride salt (170 mg, 0.43 mmol) was stirred in a mixture of saturated sodium bicarbonate solution (5 ml) and dichloromethane (5 ml) in an ice-bath. Acetic anhydride (2 mmol) was added dropwise, and the mixture stirred 18 hours, allowing the temperature to rise to ambient. Dichloromethane (10 ml) was added, and the mixture filtered through phase separating paper, the organic layer evaporated, and crystallised from ethanol to give the desired product (108 mg).

Workup

  1. filtrationthe mixture filtered through phase
  2. customseparating paper
  3. customthe organic layer evaporated
  4. customcrystallised from ethanol

Sources & evidence

ORD record
ord-63074f741cdc4e52baa451e226446f14
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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