Dichlorodimethylsilane → 7-Aminodeacetoxycephalosporanic acid

HRID 1579958Notes

Reaction equation

HRID 1579958 reaction equation
O(CC([NH:11][CH:12]1[C:23](=[O:24])[N:14]2[C:15]([C:20]([OH:22])=[O:21])=[C:16]([CH3:19])[CH2:17][S:18][C@H:13]12)=O)C1C=CC=CC=1.C1(NC2CCCCC2)CCCCC1.C(NC(C)C)(C)C.Cl[Si](Cl)(C)C.P(Cl)(Cl)(Cl)(Cl)Cl>C(Cl)Cl>[CH3:19][C:16]1[CH2:17][S:18][C@@H:13]2[C@H:12]([NH2:11])[C:23](=[O:24])[N:14]2[C:15]=1[C:20]([OH:22])=[O:21]

Participants

7

Reactant 5

HCID 6398DichlorodimethylsilaneHCID 7582DicyclohexylamineHCID 7912DiisopropylamineHCID 24819Phosphorus pentachlorideHCID 155734007-Phenoxyacetamido-3-methyl-3-cephem-4-carboxylic acid

Product 1

HCID 334987-Aminodeacetoxycephalosporanic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-45 °C

Procedure

7-(Phenoxyacetamido)-3-methyl-3-cephem-4-carboxylic acid (11.38 mmoles) is dissolved in 80 ml of methylene chloride. Dicyclohexylamine or diisopropylamine (13 mmoles) is added with stirring and 1.75 ml of dichlorodimethylsilane is added. After stirring for 30 minutes, the mixture is cooled to -45° C and an additional 27.77 mmoles of the same amine as used above is added followed by 3 g of finely powdered PCl5.

Workup

  1. stirringAfter stirring for 30 minutes
  2. additionabove is added

Sources & evidence

ORD record
ord-7bfcc8b0f6f04df4b0d800fcb15d045b
Source dataset
uspto-grants-1976_01
Patent number
US03932392

Reaction notes

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