Acetyl chloride → HCID 68133057, compound

HRID 1580512Notes

Reaction equation

HRID 1580512 reaction equation
[C:1]([C:4]1[O:32][C:7]([CH2:8][C:9]2[CH2:10][S:11](=O)[C@@H:12]3[C@H:19]([NH:20][C:21](=[O:29])[CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:18](=[O:30])[N:13]3[C:14]=2[C:15]([OH:17])=[O:16])=[CH:6][CH:5]=1)([OH:3])=[O:2].C(Cl)(=O)C>CN(C)C=O>[C:1]([C:4]1[O:32][C:7]([CH2:8][C:9]2[CH2:10][S:11][C@@H:12]3[C@H:19]([NH:20][C:21](=[O:29])[CH2:22][C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:18](=[O:30])[N:13]3[C:14]=2[C:15]([OH:17])=[O:16])=[CH:6][CH:5]=1)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 68134509HCID 68134509, compound

Product 1

HCID 68133057HCID 68133057, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1.3 g of crude 3-(5-carboxy-furfuryl)-7β-phenylacetylamino-ceph-3-em-4-carboxylic acid 1-oxide and 1.7 g of tin-II-chloride in 20 ml of dimethylformamide are added dropwise under anhydrous conditions 6 ml of acetic acid chloride, the temperature being maintained at 0°-5°. The reaction mixture is subsequently stirred for 2 hours and worked up in a conventional manner for free acids (see Example 78). Chromatography of the crude product (silica gel, washed with hydrochloric acid; elution with a 4:1-mixture of methylene chloride and ethyl acetate) and subsequent crystallisation from methyl acetate yield the 3-(5-carboxy-furfuryl)-7β-phenylacetylamino-ceph-3-em-4-carboxylic acid, m.p. 183°-186°; thin-layer chromatogram (silica gel); Rf = 0.24 (system: n-butanol/ethanol/water 40:10:50) and Rf = 0.55 (system: chloroform/methanol 1:1); infrared absorption spectrum (in mineral oil): characteristic bands at: 2,96μ, 3,18μ, 5,65μ, 5,73μ and 5,90μ.

Workup

  1. temperaturethe temperature being maintained at 0°-5°
  2. washChromatography of the crude product (silica gel, washed with hydrochloric acid
  3. washelution with a 4
  4. custom1-mixture of methylene chloride and ethyl acetate) and subsequent crystallisation from methyl acetate

Sources & evidence

ORD record
ord-d68c6a3fa8aa4ff5917f8c3a09597226
Source dataset
uspto-grants-1976_01
Patent number
US03932465

Reaction notes

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