2-Chloroethyl methyl ether → N-[[(5S)-3-[3-fluoro-4-(2-methoxyethylsulfanyl)phenyl]-2-oxo-oxazolidin-5-yl]methyl]acetamide

HRID 1979278Notes

Reaction equation

HRID 1979278 reaction equation
[C:1]([NH:4][CH2:5][C@@H:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:17]=[CH:16][C:15]([S:18][C:19]([C:32]3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[C:14]([F:38])[CH:13]=2)[CH2:7]1)(=[O:3])[CH3:2].[CH3:39][O:40]CCCl>CN1CCCC1=O>[C:1]([NH:4][CH2:5][C@@H:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:17]=[CH:16][C:15]([S:18][CH2:19][CH2:32][O:40][CH3:39])=[C:14]([F:38])[CH:13]=2)[CH2:7]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 123162-Chloroethyl methyl etherHCID 229661975-(S)-Acetamidomethyl-3-[4'-triphenylmethylthio-3'-fluorophenyl]oxazolidine-2-one

Product 1

HCID 485759N-[[(5S)-3-[3-fluoro-4-(2-methoxyethylsulfanyl)phenyl]-2-oxo-oxazolidin-5-yl]methyl]acetamide

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Prepared according to Method B of the General Procedures for Preparation of 5-(S)-(N-Acylaminomethyl)-3-[4′-(substituted)thio-3′-fluorophenyl]oxazoli-dine-2-ones from 5-(S)-acetamidomethyl-3-[4′-(triphenylmethyl)thio-3′-fluorophenyl]oxazolidine-2-one with 2-chloroethyl methyl ether (0.036 g, 0.38 mmol) in N-methylpyrrolidine-2-one (1 mL). The synthesis was performed at r.t. for 2 h. The crude product was purified by TLC (eluent: 10% methanol in dichloromethane). Yield 0.034 g (52%). MS (m/z): 343 [M+H]+. 1H NMR.

Workup

  1. customPrepared
  2. customThe crude product was purified by TLC (eluent: 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-ff6a05813f3f47be87935f4d9f94502f
Source dataset
uspto-grants-2001_05
Patent number
US06239152B1

Reaction notes

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