Ethyl Acetate → HCID 88500618, compound

HRID 1708892Notes

Reaction equation

HRID 1708892 reaction equation
[Cl:1][C:2]1[S:6][C:5]([NH:7]C(=O)CCl)=[N:4][C:3]=1/[C:12](=[N:36]/[O:37][CH3:38])/[C:13]([NH:15][C@@H:16]1[C:34](=[O:35])[N:18]2[C:19]([C:31]([OH:33])=[O:32])=[C:20]([CH2:23][O:24][C:25](=[O:30])[CH2:26][C:27](=[O:29])[CH3:28])[CH2:21][S:22][C@H:17]12)=[O:14].CNC(=S)[S-].[Na+].C(OCC)(=O)C>O.O1CCCC1>[NH2:7][C:5]1[S:6][C:2]([Cl:1])=[C:3](/[C:12](=[N:36]/[O:37][CH3:38])/[C:13]([NH:15][C@@H:16]2[C:34](=[O:35])[N:18]3[C:19]([C:31]([OH:33])=[O:32])=[C:20]([CH2:23][O:24][C:25](=[O:30])[CH2:26][C:27](=[O:29])[CH3:28])[CH2:21][S:22][C@H:17]23)=[O:14])[N:4]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 5366415Metam-sodiumHCID 88500698HCID 88500698, compound

Product 1

HCID 88500618HCID 88500618, compoundYield 88.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 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-fb2f3fc939ea4601914e6227eda9340a
Source dataset
uspto-grants-1990_08
Patent number
US04946837

Reaction notes

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