1H-Isoindole-1,3(2H)-dione, 2-(trimethylsilyl)- → HCID 54504252, compound

HRID 1658816Notes

Reaction equation

C[Si](C)(C)N1C(=O)C2=CC=CC=C2C1=O.C[Si](C)(C)[O:18][C:19]([CH:21]([N:25]1[CH:28]([S:29][N:30]2[C:34](=[O:35])[C:33]3=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]3[C:31]2=[O:40])[CH:27]([NH:41][C:42](=[O:51])[CH2:43][O:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:26]1=[O:52])[C:22]([CH3:24])=[CH2:23])=[O:20]>CC(N(C)C)=O>[C:19]([CH:21]([N:25]1[CH:28]([S:29][N:30]2[C:34](=[O:35])[C:33]3=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]3[C:31]2=[O:40])[CH:27]([NH:41][C:42](=[O:51])[CH2:43][O:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:26]1=[O:52])[C:22]([CH3:24])=[CH2:23])([OH:20])=[O:18]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1.8 g (5 mmoles) of phenoxymethylpenicillin-S-sulphoxide and 6.6 g (30 mmoles) of N-trimethylsilylphthalimide in 35 ml of dimethylacetamide was heated at 100° C for 2 hours. The reaction mixture (containing 1-(1-trimethylsilyloxycarbonyl-2-methylprop-2-enyl)-3-phenoxyacetamido-4-phthalimidothio-azetidin-2-one) was evaporated to dryness, treated with 30 ml of dichloromethane and filtered. The filtrate was concentrated and purified by chromatography on a silica gel column impregnated with 1% acetic acid, using a 4:1 (v/v) mixture of toluene and acetone with 0.5% acetic acid as an eluent. There was obtained 1-(1-carboxy-2-methylprop-2-enyl)-3-phenoxyacetamido-4-phthalimidothio-azetidin-2-one. Yield: 1.11 g (2.24 mmoles) or 45%.

Workup

customwas evaporated to dryness
additiontreated with 30 ml of dichloromethane
filtrationfiltered
concentrationThe filtrate was concentrated
custompurified by chromatography on a silica gel column
additiona 4:1 (v/v) mixture of toluene and acetone with 0.5% acetic acid as an eluent

Sources & evidence

ORD record: ord-a9bf556bf5054d86b3d14177373a636d
Source dataset: uspto-grants-1976_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03966738

Reaction notes

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