Cephalothin → HCID 14831642, compound

HRID 1657392Notes

Reaction equation

HRID 1657392 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:16]([NH:17][C:18](=[O:25])[CH2:19][C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)[C:15](=[O:26])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[CH3:2].[CH2:27](N)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.N(OCC(C)C)=O>C(#N)C.CC(N(C)C)=O>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:16]([NH:17][C:18](=[O:25])[CH2:19][C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)[C:15](=[O:26])[N:10]2[C:11]=1[C:12]([O:14][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:13])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6024CephalothinHCID 7504BenzylamineHCID 10958Isobutyl nitrite

Product 1

HCID 14831642HCID 14831642, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 3-acetoxymethyl-7β-(2-thienylacetamido) ceph-3-em-4-carboxylic acid (3.96 g., 10 m. moles) in acetonitrile (70 ml) and dimethylacetamide (5 ml) was added benzylamine (1.28 g., 12 m. moles) and isobutyl nitrite (2.47 g., 24 m. moles) and the mixture heated to 45° over 2 hours. Initially a solid formed in the mixture but with vigorous stirring it had all dissolved after 1-1.25 hours as the reaction proceeded. After removal of the solvent in vacuo, the gum was taken up in ethyl acetate (50 ml) washed with dilute H2SO4 (25 ml.), 5% NaHCO3 solution (50 ml.) and water (50 ml.), and the organic residue after evaporation of the organic solvent crystallised from hot isopropanol to yield the title ester (2.40 g., 42% based on the input acid) m.pt. 135° - 139°. T.l.c. indicated the presence of some trace impurities.

Workup

  1. temperaturethe mixture heated to 45° over 2 hours
  2. customInitially a solid formed in the mixture
  3. dissolutionall dissolved after 1-1.25 hours as the reaction
  4. customAfter removal of the solvent in vacuo
  5. washwashed with dilute H2SO4 (25 ml.), 5% NaHCO3 solution (50 ml.) and water (50 ml.)
  6. customthe organic residue after evaporation of the organic solvent
  7. customcrystallised from hot isopropanol

Sources & evidence

ORD record
ord-2d227e8396e047df9ebffd18016a8d0c
Source dataset
uspto-grants-1976_06
Patent number
US03960843

Reaction notes

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