Formic Acid → HCID 13892058, compound

HRID 1903569Notes

Reaction equation

HRID 1903569 reaction equation
C([BH3-])#N.[Na+].[CH:5]([O:18][C:19]([C:21]1[N:26]2[C:27](=[O:40])[C@@H:28]([NH:29][C:30](=[O:39])[CH2:31][O:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C@H:25]2[S:24][CH2:23][C:22]=1N1CCOCC1)=[O:20])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(O)=O>O1CCCC1.C(Cl)Cl.C(O)(=O)C>[CH:5]([O:18][C:19]([C:21]1[N:26]2[C:27](=[O:40])[C@@H:28]([NH:29][C:30](=[O:39])[CH2:31][O:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C@H:25]2[S:24][CH2:23][CH:22]=1)=[O:20])([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

7

Reactant 3

HCID 284Formic AcidHCID 5003444Sodium cyanoborohydrideHCID 44151031N-{2-[(Diphenylmethoxy)carbonyl]-3-(morpholin-4-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-7-yl}-2-phenoxyethanimidic acid

Product 1

HCID 13892058HCID 13892058, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.05 g of sodium cyanoborohydride in 30 ml of tetrahydrofurane is added dropwise over 20 minutes to a solution of 5.86 g (10 mmols) of 7β-phenoxyacetylamino-3-morpholino-3-cephem-4-carboxylic acid benzhydryl ester in 50 ml of methylene chloride and 50 ml of glacial acetic acid, whereupon vigorous evolution of gas occurs. Then 20 ml of formic acid are added and the reaction mixture is stirred for 16 hours at room temperature. For working up, the reaction mixture is diluted with 300 ml of methylene chloride and the organic phase is washed four times with 100 ml of water, then dried over sodium sulfate. The solvent is distilled off in vacuo. The almost colourless crude product is chromatographed on silica gel with toluene/ethyl acetate (9:1), affording pure 7β-phenoxyacetylamino-3-cephem-4-carboxylic acid benzhydryl ester.

Workup

  1. washthe organic phase is washed four times with 100 ml of water
  2. dry with materialdried over sodium sulfate
  3. distillationThe solvent is distilled off in vacuo
  4. customThe almost colourless crude product is chromatographed on silica gel with toluene/ethyl acetate (9:1)

Sources & evidence

ORD record
ord-faf854d518c84ecfac27c7f67d928302
Source dataset
uspto-grants-1984_03
Patent number
US04436903

Reaction notes

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