2,6-Di-tert-butylpyridine → 5-(S)-Acetamidomethyl-3-[4'-formamido-3'-fluorophenyl]oxazolidine-2-one

HRID 351868Notes

Reaction equation

HRID 351868 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]([NH2:18])=[C:14]([F:19])[CH:13]=2)[CH2:7]1)(=[O:3])[CH3:2].[CH:20](OC1C=CC([N+]([O-])=O)=CC=1)=[O:21].C(C1C=CC=C(C(C)(C)C)N=1)(C)(C)C>C1COCC1>[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]([NH:18][CH:20]=[O:21])=[C:14]([F:19])[CH:13]=2)[CH2:7]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 685102,6-Di-tert-butylpyridineHCID 746284-Nitrophenyl formateHCID 10778218(S)-N-[3-[3-Fluoro-4-aminophenyl]-2-oxo-5-oxazolidinyl]methylacetamide

Product 1

HCID 229661905-(S)-Acetamidomethyl-3-[4'-formamido-3'-fluorophenyl]oxazolidine-2-oneYield 85.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-(S)-acetamidomethyl-3-[4′-amino-3′-fluorophenyl]-oxazolidine-2-one (0.200 g, 0.748 mmol), p-nitrophenyl formate (0.188 g, 1.12 mmol), and 2,6-di-(tert-butyl)pyridine (0.336 mL, 1.50 mmol) in THF (4 mL) was stirred at 65° C. overnight. Solvent was removed under vacuum and the residue purified by PTLC (30% acetone in DCM) to give product as a white solid (0.188 g, 85%). M.p. 196-8° C.; MS (m/z): [M+H]+=296.

Workup

  1. customSolvent was removed under vacuum
  2. customthe residue purified by PTLC (30% acetone in DCM)

Sources & evidence

ORD record
ord-77e4da8371a04de5a609669748cff5be
Source dataset
uspto-grants-2004_06
Patent number
US06743811B2

Reaction notes

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