Cephalothin → HCID 13065698, compound

HRID 1657390Notes

Reaction equation

HRID 1657390 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].N(OC(C)C)=O.[C:33]1([CH:39](N)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>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][CH:39]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:13])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6024CephalothinHCID 7036BenzhydrylamineHCID 10929Isopropyl nitrite

Product 1

HCID 13065698HCID 13065698, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 31374DimethylacetamideSolvent

Procedure

3-Acetoxymethyl-7β-(2-thienylacetamido)ceph-3-em-4-carboxylic acid (3.96 g, 10 m.moles) was dissolved in acetonitrile (50 ml) and dimethylacetamide (5ml). To this solution was added a mixture of isopropyl nitrite (2.4 g, 27 m.moles) and diphenylmethylamine (2.21 g, 12 m.moles) dissolved-suspended in acetonitrile (20 ml). The resulting slurry was stirred for 3 hours at 35°, after which time a solution resulted. The solvents were removed in vacuo and the gum redissolved in chloroform (50 ml). The resulting solution was washed with 5% sodium bicarbonate solution (50 ml), then water (50 ml) and the chloroform removed in vacuo. The gum was crystallised from hot isopropyl alcohol (28 ml), the crystals washed with cold isopropyl alcohol (25 ml) and then dried in vacuo at room temperature to give the title compound. Yield 3.19 g (56.8% based on the input acid); m. pt. and mixed m. pt. 140° - 140.5° with an authentic sample of the ester. The bicarbonate extract was washed with ethyl acetate (10 ml) and then acidified with 2N sulphuric acid at 5° to pH 1.2. The suspension was stirred for 30 minutes, filtered and washed with cold water (70 ml). The recovered starting material was dried in vacuo at room temperature, (0.9 g, single spot on t.l.c. by u.v. detection).

Workup

  1. additionTo this solution was added
  2. customafter which time a solution resulted
  3. customThe solvents were removed in vacuo
  4. dissolutionthe gum redissolved in chloroform (50 ml)
  5. washThe resulting solution was washed with 5% sodium bicarbonate solution (50 ml)
  6. customwater (50 ml) and the chloroform removed in vacuo
  7. customThe gum was crystallised from hot isopropyl alcohol (28 ml)
  8. washthe crystals washed with cold isopropyl alcohol (25 ml)
  9. customdried in vacuo at room temperature

Sources & evidence

ORD record
ord-eab8144542e448f6babc50a324ff11ac
Source dataset
uspto-grants-1976_06
Patent number
US03960843

Reaction notes

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