Hydrochloric Acid → (6R,7R)-7-[[(2Z)-2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-methoxyiminoacetyl]amino]-8-oxo-3-(3-oxobutanoyloxymethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 978415Notes

Reaction equation

HRID 978415 reaction equation
[NH2:1][C@@H:2]1[C:20](=[O:21])[N:4]2[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH2:9][O:10][C:11](=[O:16])[CH2:12][C:13](=[O:15])[CH3:14])[CH2:7][S:8][C@H:3]12.C(=O)([O-])O.[Na+].Cl.[Cl:28][CH2:29][C:30]([NH:32][C:33]1[S:34][CH:35]=[C:36](/[C:38](=[N:42]/[O:43][CH3:44])/[C:39](Cl)=[O:40])[N:37]=1)=[O:31].Cl>O1CCCC1.O>[Cl:28][CH2:29][C:30]([NH:32][C:33]1[S:34][CH:35]=[C:36](/[C:38](=[N:42]/[O:43][CH3:44])/[C:39]([NH:1][C@@H:2]2[C:20](=[O:21])[N:4]3[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH2:9][O:10][C:11](=[O:16])[CH2:12][C:13](=[O:15])[CH3:14])[CH2:7][S:8][C@H:3]23)=[O:40])[N:37]=1)=[O:31]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 117819897beta-Amino-3(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acidHCID 12884125(2Z)-2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-methoxyiminoacetyl chloride;hydrochloride

Product 1

HCID 13457838(6R,7R)-7-[[(2Z)-2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-methoxyiminoacetyl]amino]-8-oxo-3-(3-oxobutanoyloxymethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidYield 97.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a mixture of 500 ml of tetrahydrofuran and 500 ml of water is suspended 157 g of 7β-amino-3-(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acid. To the suspension is added little by little 141 g of sodium hydrogen carbonate with stirring. To the mixture is added 150 g of 2-(2-chloroacetamidothiazol-4-yl)-2(Z)-methoxyiminoacetyl chloride hydrochloride at 5° C., during 20 minutes with stirring, and the mixture was stirred for further one hour. After completion of the reaction, the reaction mixture is adjusted to pH 3.0 with 10% hydrochloric acid, and extracted twice with 1 l portions of a mixture is ethyl acetate-tetrahydrofuran (1:1). The extract is dried over anhydrous magnesium sulfate, and then the solvent is evaporated off under reduced pressure to leave colorless powder, which is triturated with 200 ml of ethyl acetate and collected by filtration to afford 253 g of the above-identified compound.

Workup

  1. stirringduring 20 minutes with stirring
  2. stirringthe mixture was stirred for further one hour
  3. customAfter completion of the reaction
  4. extractionextracted twice with 1 l portions of a mixture
  5. dry with materialThe extract is dried over anhydrous magnesium sulfate
  6. customthe solvent is evaporated off under reduced pressure
  7. customto leave colorless powder, which
  8. customis triturated with 200 ml of ethyl acetate
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-91b67af5782e41779fcabcac6257720d
Source dataset
uspto-grants-1987_05
Patent number
US04665065

Reaction notes

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