Acetic Anhydride → (5S,7S)-5-(4-Cyanobenzyl)-3-(3,5-dichlorophenyl)-7-acetylamino-1,3-diazabicyclo[3.3.0]octane-2,4-dione

HRID 2223330Notes

Reaction equation

[C:1]([C:3]1[CH:28]=[CH:27][C:6]([CH2:7][C@@:8]23[CH2:15][C@H:14]([NH2:16])[CH2:13][N:12]2[C:11](=[O:17])[N:10]([C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=2)[C:9]3=[O:26])=[CH:5][CH:4]=1)#[N:2].[C:29](OC(=O)C)(=[O:31])[CH3:30]>C1COCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][C@@:8]23[CH2:15][C@H:14]([NH:16][C:29](=[O:31])[CH3:30])[CH2:13][N:12]2[C:11](=[O:17])[N:10]([C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=2)[C:9]3=[O:26])=[CH:27][CH:28]=1)#[N:2]

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of (5S,7S)-5-(4-cyanobenzyl)-3-(3,5-dichlorophenyl)-7-amino-1,3-diazabicyclo[3.3.0]octane-2,4-dione (78.5 mg) in THF (5 mL) was added acetic anhydride (1.0 mL). The reaction mixture was stirred for 2 hours at 45° C., and the mixture was concentrated and purified by preparative thin-layer chromatography (silica gel; CH2Cl2) to afford the titled compound (84 mg). MS (m/z) 478.8 (MNa+).

Workup

concentrationthe mixture was concentrated
custompurified by preparative thin-layer chromatography (silica gel; CH2Cl2)

Sources & evidence

ORD record: ord-41f028250b5a4cb1ad1bec24eeabdc6e
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07375128B2

Reaction notes

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