Acetic Acid → HCID 131712337, compound

HRID 1758425Notes

Reaction equation

HRID 1758425 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:35][O:36][CH2:37][C:38](=[O:40])[NH2:39])[C:10]([NH:12][CH:13]2[C:33](=[O:34])[N:15]3[C:16]([C:20]([O:22]CC4C=CC([N+]([O-])=O)=CC=4)=[O:21])=[CH:17][CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=[O:2].C(O)(=O)C.CO.O>[C].[Pd].O1CCCC1>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:35][O:36][CH2:37][C:38](=[O:40])[NH2:39])[C:10]([NH:12][CH:13]2[C:33](=[O:34])[N:15]3[C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=[O:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 962WaterHCID 131712336HCID 131712336, compound

Product 1

HCID 131712337HCID 131712337, compoundYield 49.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-carbamoylmethoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 2.4 g.), 10% palladium-carbon (0.96 g.), acetic acid (0.17 ml.), methanol (9.6 ml.), water (1.7 ml.) and tetrahydrofuran (24 ml.) was subjected to catalytic reduction under ordinary pressure for 3 hours. After filtration, the filtrate was concentrated in vacuo. Water and ethyl acetate were added to the residue and adjusted to pH 7.5 with sodium bicarbonate. After filtration, the filtrate was washed with ethyl acetate and diethyl ether in turn, adjusted to pH 1.0 with 10% hydrochloric acid and stirred under ice-cooling for 20 minutes. The precipitates were collected by filtration, washed with water, and dried to give 7-[2-(2-formamidothiazol-4-yl)-2-carbamoylmethoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 0.92 g.).

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionWater and ethyl acetate were added to the residue
  4. filtrationAfter filtration
  5. washthe filtrate was washed with ethyl acetate and diethyl ether in turn
  6. temperaturecooling for 20 minutes
  7. filtrationThe precipitates were collected by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-e4ce4c1c18b54d85a62720c71f818095
Source dataset
uspto-grants-1983_02
Patent number
US04372952

Reaction notes

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