O-(Trimethylsilyl)hydroxylamine → HCID 178474861, compound

HRID 2305669Notes

Reaction equation

HRID 2305669 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-3ef7a47c27b54de18feeea8b320058cf
Source dataset
uspto-grants-2002_08
Patent number
US06441005B1

Reaction notes

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