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

HRID 893905Notes

Reaction equation

HRID 893905 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-2c94f8002a8d45abaefc06c4bbc6b555
Source dataset
uspto-grants-1981_08
Patent number
US04282145

Reaction notes

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