Acetyl chloride → HCID 131709952, compound

HRID 1580511Notes

Reaction equation

HRID 1580511 reaction equation
[Cl:1][C:2]([Cl:41])([Cl:40])[CH2:3][O:4][C:5]([C:7]1[N:12]2[C:13](=[O:24])[C@@H:14]([C:15](=[O:23])[CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C@H:11]2[S:10](=O)[CH:9]([NH2:26])[C:8]=1[CH2:27][C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]([O:38][CH3:39])=[CH:30][CH:29]=1)=[O:6].C1S(=O)(=O)CCC1.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(Cl)(=O)C.C(=O)([O-])O.[Na+]>C(#N)C>[Cl:40][C:2]([Cl:1])([Cl:41])[CH2:3][O:4][C:5]([C:7]1[N:12]2[C:13](=[O:24])[C@@H:14]([C:15](=[O:23])[CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C@H:11]2[S:10][CH:9]([NH2:26])[C:8]=1[CH2:27][C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]([O:38][CH3:39])=[CH:30][CH:29]=1)=[O:6]

Participants

7

Reactant 5

HCID 6367Acetyl chloride2×HCID 24489Sodium DithioniteHCID 31347SulfolaneHCID 516892Sodium BicarbonateHCID 131709953HCID 131709953, compound

Product 1

HCID 131709952HCID 131709952, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 0.317 g of 3-(4-methoxy-1-naphthylmethyl)-7β-phenylacetyl-amino-ceph-3-em-4-carboxylic acid 2,2,2-trichloroethyl ester 1-oxide in 10 ml of a 9:1-mixture of tetramethylenesulphone and acetonitrile is treated with 0.250 g of sodium dithionite. The mixture is cooled to 0° and agitated in an ultrasonics bath, then treated with 0.275 g of acetic acid chloride. The mixture is allowed to react for 30 minutes and an equal amount of acetic acid chloride is again added. After a further 30 minutes, the reaction mixture is poured out onto a 5% aqueous sodium hydrogen carbonate solution. After extraction with diethyl ester, the combined organic extracts are washed with water and a saturated aqueous sodium chloride solution, dried over magnesium sulphate and evaporated under reduced pressure. The residue is chromatographed on 10 g of silica gel, elution being carried out with methylene chloride and fractions of 50 ml being taken. Fractions 3 and 4 yield the 3-(4-methoxy-1-naphthylmethyl)-7β-phenylacetyl-amino-ceph-3-em-4-carboxylic acid 2,2,2-trichloroethyl ester, which after crystallisation from a mixture of ethyl acetate and diethyl ether melts at 164°-165°; thin-layer chromatogram (silica gel): Rf = 0.73 (system: toluene/ethyl acetate 1:1) and Rf = 0.59 (system: toluene/acetone 4:1); infrared absorption spectrum (in mineral oil): characteristic bands at 2,99μ, 5,63μ, 5,75μ, 5,99μ, 6,12μ, 6,29μ and 6,53μ.

Workup

  1. temperatureThe mixture is cooled to 0°
  2. customto react for 30 minutes
  3. extractionAfter extraction with diethyl ester
  4. washthe combined organic extracts are washed with water
  5. dry with materiala saturated aqueous sodium chloride solution, dried over magnesium sulphate
  6. customevaporated under reduced pressure
  7. customThe residue is chromatographed on 10 g of silica gel, elution

Sources & evidence

ORD record
ord-a1ec5139e3844d008cf005ad7f0910a5
Source dataset
uspto-grants-1976_01
Patent number
US03932465

Reaction notes

Loading…