Acetic Acid → 7-[2-(2,3-Dihydro-1,4-oxathiin-6-yl)-2-n-propoxyiminoacetamido]-3-cephem-4-carboxylic acid

HRID 1758072Notes

Reaction equation

HRID 1758072 reaction equation
[O:1]1[C:6]([C:7](=[N:33][O:34][CH2:35][CH2:36][CH3:37])[C:8]([NH:10][CH:11]2[C:31](=[O:32])[N:13]3[C:14]([C:18]([O:20]CC4C=CC([N+]([O-])=O)=CC=4)=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])=[CH:5][S:4][CH2:3][CH2:2]1.O1CCCC1.CO.C(O)(=O)C>[C].[Pd].O>[O:1]1[C:6]([C:7](=[N:33][O:34][CH2:35][CH2:36][CH3:37])[C:8]([NH:10][CH:11]2[C:31](=[O:32])[N:13]3[C:14]([C:18]([OH:20])=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])=[CH:5][S:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 8028TetrahydrofuranHCID 1317120154-Nitrobenzyl 7-[2-(2,3-dihydro-1,4-oxathiin-6-yl)-2-n-propoxyiminoacetamido]-3-cephem-4-carboxylate

Product 1

HCID 1317120167-[2-(2,3-Dihydro-1,4-oxathiin-6-yl)-2-n-propoxyiminoacetamido]-3-cephem-4-carboxylic acidYield 51.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolvent

Procedure

4-Nitrobenzyl 7-[2-(2,3-dihydro-1,4-oxathiin-6-yl)-2-n-propoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 6.7 g.), tetrahydrofuran (200 ml.), methanol (67 ml.), acetic acid (2 ml.), water (6 ml.) and 10% palladium-carbon (3.3 g.) were treated in a similar manner to that of Example 18-(2) to give 7-[2-(2,3-dihydro-1,4-oxathiin-6-yl)-2-n-propoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 2.59 g.).

Sources & evidence

ORD record
ord-ecf99d955a8745b78d2ab082cb259da3
Source dataset
uspto-grants-1983_02
Patent number
US04371531

Reaction notes

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