HCID 15549555, compound → HCID 86585623, compound

HRID 651216Notes

Reaction equation

HRID 651216 reaction equation
[C:1]([CH2:3][S:4]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:23][C@H:22]([CH2:24][NH:25][C:26](=[O:28])[CH3:27])[O:21][C:20]3=[O:29])=[CH:15][C:14]=2[F:30])[CH2:9][CH2:8]1)(=[O:6])=[O:5])#[N:2].C1C=C([O:37]O)C(C(O)=O)=C(C(O)=O)C=1>CO>[C:1]([CH2:3][S:4]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:23][C@@H:22]([CH2:24][NH+:25]([O-:37])[C:26](=[O:28])[CH3:27])[O:21][C:20]3=[O:29])=[CH:15][C:14]=2[F:30])[CH2:9][CH2:8]1)(=[O:6])=[O:5])#[N:2]

Participants

4

Reactant 2

HCID 15549555HCID 15549555, compoundHCID 198097063-Hydroperoxyphthalic acid

Product 1

HCID 86585623HCID 86585623, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-N-[[3-[4-[4-[(cyanomethyl)sulfonyl]-1-piperazinyl]-3-fluorophenyl]2-oxo-5-oxazolidinyl]methyl]acetamide (VIII-G, R1=COCH3, R9=NCCH2, X1=F, X2=H) (0.550 g) is dissolved in 15 mL of methanol. Monoperoxyphthalic acid, magnesium salt hexahydrate (80% pure, 0.616 g) is added and the reaction is stirred at room temperature for 4 hours. The reaction is then filtered and the filtrate is concentrated to afford an oil. This oil is chromatographed on silica gel using 10% methanol (saturated with ammonia) in chloroform as eluent to afford 0.42 g of the N-oxide.

Workup

  1. filtrationThe reaction is then filtered
  2. concentrationthe filtrate is concentrated
  3. customto afford an oil
  4. customThis oil is chromatographed on silica gel using 10% methanol (saturated with ammonia) in chloroform as eluent

Sources & evidence

ORD record
ord-d10935de9d0d4563b58caa7922f4e9a2
Source dataset
uspto-grants-2001_08
Patent number
US06277985B1

Reaction notes

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