Pyridine → 5-(S)-Acetamidomethyl-3-[4'-methylsulfinyl-3'-fluorophenyl]oxazolidine-2-one

HRID 351895Notes

Reaction equation

HRID 351895 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].N1C=CC=CC=1.[NH2:14][CH2:15][C@@H:16]1[O:20][C:19](=[O:21])[N:18]([C:22]2[CH:27]=[CH:26][C:25]([S:28]([CH3:30])=[O:29])=[C:24]([F:31])[CH:23]=2)[CH2:17]1>C(Cl)Cl>[C:1]([NH:14][CH2:15][C@@H:16]1[O:20][C:19](=[O:21])[N:18]([C:22]2[CH:27]=[CH:26][C:25]([S:28]([CH3:30])=[O:29])=[C:24]([F:31])[CH:23]=2)[CH2:17]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 229662005-(S)-aminomethyl-3-[4'-methylsulfinyl-3'-fluorophenyl]oxazolidine-2-one

Product 1

HCID 229661925-(S)-Acetamidomethyl-3-[4'-methylsulfinyl-3'-fluorophenyl]oxazolidine-2-oneYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (0.173 ml, 1.83 mmol) and pyridine (0.296 ml, 3.67 mmol) were added to a solution of 5-(S)-aminomethyl-3-[4′-methylsulfinyl-3′-fluorophenyl]oxazolidine-2-one (0.100 g, 0.367 mmol) in DCM (3 ml). The reaction mixture was stirred for 4 h at r.t. and then evaporated to dryness under vacuum. The residue was purified by PTLC (10% methanol in DCM) to give product as a white solid (0.115 g, 99%). M.p. 143-5° C. MS (m/z): [M+H]+=315.

Workup

  1. customevaporated to dryness under vacuum
  2. customThe residue was purified by PTLC (10% methanol in DCM)

Sources & evidence

ORD record
ord-5d948723626b4791a8f0936a3c2f6602
Source dataset
uspto-grants-2004_06
Patent number
US06743811B2

Reaction notes

Loading…