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

HRID 1733751Notes

Reaction equation

HRID 1733751 reaction equation
[O:1]1[C:6]([C:7](=[N:34][O:35][CH2:36][CH2:37][CH3:38])[C:8]([NH:10][CH:11]2[C:32](=[O:33])[N:13]3[C:14]([C:19]([O:21]CC4C=CC([N+]([O-])=O)=CC=4)=[O:20])=[C:15]([Cl:18])[CH2:16][S:17][C@H:12]23)=[O:9])=[CH:5][S:4][CH2:3][CH2:2]1.C(O)(=O)C.O.O1CCCC1>[C].[Pd].CO>[O:1]1[C:6]([C:7](=[N:34][O:35][CH2:36][CH2:37][CH3:38])[C:8]([NH:10][CH:11]2[C:32](=[O:33])[N:13]3[C:14]([C:19]([OH:21])=[O:20])=[C:15]([Cl:18])[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 962WaterHCID 8028TetrahydrofuranHCID 1317120194-Nitrobenzyl 7-[2-(2,3-dihydro-1,4-oxathiin-6-yl)-2-n-propoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate

Product 1

HCID 1317120207-[2-(2,3-Dihydro-1,4-oxathiin-6-yl)-2-n-propoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acidYield 43%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

4-Nitrobenzyl 7-[2-(2,3-dihydro-1,4-oxathiin-6-yl)-2-n-propoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate (syn isomer, 7.0 g.), acetic acid (2 ml.), water (10 ml.), 10% palladium-carbon (3.5 g.) tetrahydrofuran (100 ml.) and methanol (100 ml.) were treated in a similar manner to that of Example 19-(2). The obtained crystals were recrystallized from methylene chloride (20 ml.) to give 7-[2-(2,3-dihydro-1,4-oxathiin-6-yl)-2-n-propoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acid (syn isomer, 2.31 g.).

Workup

  1. customThe obtained crystals were recrystallized from methylene chloride (20 ml.)

Sources & evidence

ORD record
ord-20f0b4609985424c88b02f9a1eccb804
Source dataset
uspto-grants-1980_12
Patent number
US04242510

Reaction notes

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