Ketene → HCID 178468091, compound

HRID 654981Notes

Reaction equation

HRID 654981 reaction equation
[CH2:1]([NH:8][C:9]([CH:24]([CH3:33])[CH2:25][S:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[CH:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:34]=[C:35]=[O:36]>C1(C)C=CC=CC=1>[C:35]([C:10](=[C:9]([NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:24]([CH3:33])[CH2:25][S:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=1)=[O:12])(=[O:36])[CH3:34]

Participants

4

Reactant 2

HCID 10038KeteneHCID 67833057HCID 67833057, compound

Product 1

HCID 178468091HCID 178468091, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

p-Nitrobenzyl 3-benzylamino-4-methyl-5-phenylthio-2-pentenoate (505 mg; 1 mmole) was dissolved in toluene (5 ml), and gaseous ketene was introduced therein at room temperature. After completion of the reaction, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography to give p-nitrobenzyl 2-acetyl-3-benzylamino-4-methyl-5-phenylthio-2-pentenoate.

Workup

  1. customat room temperature
  2. customAfter completion of the reaction
  3. customthe solvent was removed under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1aba8105fefd4e00922b292021d569b6
Source dataset
uspto-grants-1992_07
Patent number
US05134231

Reaction notes

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