1H-Isoindole-1,3(2H)-dione, 2-(trimethylsilyl)- → HCID 21161747, compound

HRID 1658817Notes

Reaction equation

HRID 1658817 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]([N:41]2[C:45](=[O:46])[C:44]3=[CH:47][CH:48]=[CH:49][CH:50]=[C:43]3[C:42]2=[O:51])[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]([N:41]2[C:42](=[O:51])[C:43]3=[CH:50][CH:49]=[CH:48][CH:47]=[C:44]3[C:45]2=[O:46])[C:26]1=[O:52])[C:22]([CH3:24])=[CH2:23])([OH:20])=[O:18]

Participants

4

Reactant 2

HCID 826151H-Isoindole-1,3(2H)-dione, 2-(trimethylsilyl)-HCID 21161742HCID 21161742, compound

Product 1

HCID 21161747HCID 21161747, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 1.1 g (3 mmoles) of 6-phthalimidopenicillanic acid-R-sulphoxide in 20 ml of dimethylacetamide was treated with 4 g (18 mmoles) of N-trimethylsilylphthalimide at 100° C. After 4 hours the mixture (containing 1-(1-trimethylsilyloxycarbonyl-2-methylprop-2-enyl)-3-phthalimido-4-phthalimidothio-azetidin-2-one) was concentrated, the residue was dissolved in 30 ml of dichloromethane and the solution was filtered. The filtrate was purified by chromatography on a silica gel column impregnated with 1% acetic acid, using a 4:1 (v/v) mixture of toluene and acetone containing 0.5% acetic acid as an eluent. There were obtained 100 mg of 7-phthalimido-Δ3 -desacetoxycephalosporanic acid and 210 mg of 1-(1-carboxy-2-methylprop-2-enyl)-3-phthalimido-4-phthalimidothio-azetidin-2-one contaminated with dimethylacetamide.

Workup

  1. concentrationwas concentrated
  2. dissolutionthe residue was dissolved in 30 ml of dichloromethane
  3. filtrationthe solution was filtered
  4. customThe filtrate was purified by chromatography on a silica gel column
  5. additiona 4:1 (v/v) mixture of toluene and acetone containing 0.5% acetic acid as an eluent

Sources & evidence

ORD record
ord-45f245dfabd04895a84289fca9cf274b
Source dataset
uspto-grants-1976_06
Patent number
US03966738

Reaction notes

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