Methanol → 7-[2-(2,3-Dihydro-1,4-dithiin-5-yl)-2-methoxyiminoacetamido-]-3-chloro-3-cephem-4-carboxylic acid

HRID 1758078Notes

Reaction equation

HRID 1758078 reaction equation
[S:1]1[CH:6]=[C:5]([C:7](=[N:34][O:35][CH3:36])[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])[S:4][CH2:3][CH2:2]1.O1CCCC1.CO.O>[C].[Pd].C(O)(=O)C>[S:1]1[CH:6]=[C:5]([C:7](=[N:34][O:35][CH3:36])[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])[S:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 8028TetrahydrofuranHCID 1317120214-Nitrobenzyl 7-[2-(2,3-dihydro-1,4-dithiin-5yl)-2-methoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate

Product 1

HCID 1317120227-[2-(2,3-Dihydro-1,4-dithiin-5-yl)-2-methoxyiminoacetamido-]-3-chloro-3-cephem-4-carboxylic acidYield 41.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

4-Nitrobenzyl 7-[2-(2,3-dihydro-1,4-dithiin-5-yl)-2-methoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate (syn isomer, 5.0 g.), tetrahydrofuran (50 ml.), methanol (30 ml.), 10% palladium-carbon (2 g.), water (7 ml.) and acetic acid (0.7 ml.) were treated in a similar manner to that of Example 19-(2) to give 7-[2-(2,3-dihydro-1,4-dithiin-5-yl)-2-methoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acid (syn isomer, 1.6 g.).

Sources & evidence

ORD record
ord-072f0371bf6e4f37b441497d4eb65fe4
Source dataset
uspto-grants-1983_02
Patent number
US04371531

Reaction notes

Loading…