O-(Trimethylsilyl)hydroxylamine → HCID 178474861, compound

HRID 351881

Reaction equation

HRID 351881 reaction equation
C[Si](C)(C)[O:3][NH2:4].[C:7]([NH:10][CH2:11][C@@H:12]1[O:16][C:15](=[O:17])[N:14]([C:18]2[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[C:20]([F:26])[CH:19]=2)[CH2:13]1)(=[O:9])[CH3:8]>C(O)C>[C:7]([NH:10][CH2:11][C@@H:12]1[O:16][C:15](=[O:17])[N:14]([C:18]2[CH:23]=[CH:22][C:21]([C:24](=[NH:25])[NH:4][OH:3])=[C:20]([F:26])[CH:19]=2)[CH2:13]1)(=[O:9])[CH3:8]

Participants

4

Reactant 2

HCID 2734666O-(Trimethylsilyl)hydroxylamineHCID 229661895-(S)-acetamidomethyl-3-[4'-cyano-3'-fluorophenyl]oxazolidine-2-one

Product 1

HCID 178474861HCID 178474861, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

O-Trimethylsilylhydroxylamine (0.37 ml, 3.0 mmol) and 5-(S)-acetamidomethyl-3-[4′-cyano-3′-fluorophenyl]oxazolidine-2-one (0.277 g, 1.0 mmol) in ethanol (3.0 ml) were stirred at 80° C. in a sealed reaction vial for 2.5 h. The mixture was left at r.t. for 48 h, and the crystallized product filtered, rinsed with ethanol (ca. 0.75 ml), washed with ether, and dried under vacuum. Yellow crystals. Yield 0.260 g (84%). HPLC: Rt 2.6 min. MS (m/z): [M+H]+=311.

Workup

  1. filtrationthe crystallized product filtered
  2. washrinsed with ethanol (ca. 0.75 ml)
  3. washwashed with ether
  4. customdried under vacuum

Sources & evidence

ORD record
ord-340c4767b10a46debfb353ea1607ee36
Source dataset
uspto-grants-2004_06
Patent number
US06743811B2

Linked notes

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