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

HRID 1861226Notes

Reaction equation

HRID 1861226 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]([CH:18](OC)[O:19]C)=[C:14]([F:23])[CH:13]=2)[CH2:7]1)(=[O:3])[CH3:2]>FC(F)(F)C(O)=O.ClCCl>[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]([CH:18]=[O:19])=[C:14]([F:23])[CH:13]=2)[CH2:7]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 229773135-(S)-Acetamidomethyl-3-[4'-dimethoxymethyl-3'-fluorophenyl]-oxazolidine-2-one

Product 1

HCID 229773145-(S)-Acetamidomethyl-3-[4'-formyl-3'-fluorophenyl]oxazolidine-2-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

BAL resin immobilized 5-(S)-acetamidomethyl-3-[4′dimethoxymethyl-3′-fluorophenyl]-oxazolidine-2-one (0.100 g, 0.029 mmol) was suspended in 60% trifluoroacetic acid in dichloromethane (2 ml) for 2 h at room temperature. The mixture was filtered, and supernatant was evaporated under vacuum to give the crude product. The crude product was purified by preparative HPLC to afford the desired product as an oil. Yield 4.9 mg, (60%). Rt 3.0 min. MS (m/z): 281.1 [M+H]+. 1H NMR.

Workup

  1. filtrationThe mixture was filtered
  2. customsupernatant was evaporated under vacuum
  3. customto give the crude product
  4. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-b234d22c264b44f692f8953756893661
Source dataset
uspto-grants-2003_03
Patent number
US06531470B1

Reaction notes

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