Water → HCID 88500618, compound

HRID 2232423Notes

Reaction equation

HRID 2232423 reaction equation
O.O1CCCC1.[Cl:7][C:8]1[S:12][C:11]([NH:13]C(=O)CCl)=[N:10][C:9]=1/[C:18](=[N:42]/[O:43][CH3:44])/[C:19]([NH:21][C@@H:22]1[C:40](=[O:41])[N:24]2[C:25]([C:37]([OH:39])=[O:38])=[C:26]([CH2:29][O:30][C:31](=[O:36])[CH2:32][C:33](=[O:35])[CH3:34])[CH2:27][S:28][C@H:23]12)=[O:20].CNC(=S)[S-].[Na+]>C(OCC)(=O)C>[NH2:13][C:11]1[S:12][C:8]([Cl:7])=[C:9](/[C:18](=[N:42]/[O:43][CH3:44])/[C:19]([NH:21][C@@H:22]2[C:40](=[O:41])[N:24]3[C:25]([C:37]([OH:39])=[O:38])=[C:26]([CH2:29][O:30][C:31](=[O:36])[CH2:32][C:33](=[O:35])[CH3:34])[CH2:27][S:28][C@H:23]23)=[O:20])[N:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 5366415Metam-sodiumHCID 88500698HCID 88500698, compound

Product 1

HCID 88500618HCID 88500618, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 13 ml of water and 13 ml of tetrahydrofuran is dissolved 2.94 g of 7β-[2-(5-chloro-2-chloroacetamidothiazol-4-yl)-2(Z)-methoxyiminoacetamido]-3-(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acid. To the mixture is added 1.15 g of sodium N-methyldithiocarbamate in 3 portions with stirring at room temperature for 3 hours. Ethyl acetate is added to the reaction mixture and the ethyl acetate layer is separated and discarded. The aqueous layer is acidified with concentrated hydrochloric acid and extracted with 200 ml of methyl ethyl ketone. The extract is washed with aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent is then evaporated off to give 2.28 g of the above-identified compound.

Workup

  1. customthe ethyl acetate layer is separated
  2. extractionextracted with 200 ml of methyl ethyl ketone
  3. washThe extract is washed with aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent is then evaporated off

Sources & evidence

ORD record
ord-3217906e6d714dc99c652bc41982ebdf
Source dataset
uspto-grants-1988_11
Patent number
US04788185

Reaction notes

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