Water → 1-ethoxycarbonyloxyethyl (6R)-7-[[(2Z)-2-methoxyimino-2-(1,3-thiazol-4-yl)acetyl]amino]-3-[(3-methyl-1,2,4-thiadiazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 34265Notes

Reaction equation

HRID 34265 reaction equation
[CH3:1][O:2]/[N:3]=[C:4](/[C:37]1[N:38]=[CH:39][S:40][CH:41]=1)\[C:5]([NH:7][CH:8]1[C:35](=[O:36])[N:10]2[C:11]([C:24]([O:26][CH:27]([O:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH3:28])=[O:25])=[C:12]([CH2:16][S:17][C:18]3[S:22][N:21]=[C:20]([CH3:23])[N:19]=3)[CH2:13][S:14](=O)[C@H:9]12)=[O:6].C(Cl)(=O)C.O.C(OCC)(=O)C>CN(C)C=O>[CH3:1][O:2]/[N:3]=[C:4](/[C:37]1[N:38]=[CH:39][S:40][CH:41]=1)\[C:5]([NH:7][CH:8]1[C:35](=[O:36])[N:10]2[C:11]([C:24]([O:26][CH:27]([O:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH3:28])=[O:25])=[C:12]([CH2:16][S:17][C:18]3[S:22][N:21]=[C:20]([CH3:23])[N:19]=3)[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8857Ethyl AcetateHCID 88640714HCID 88640714, compound

Product 1

HCID 886408711-ethoxycarbonyloxyethyl (6R)-7-[[(2Z)-2-methoxyimino-2-(1,3-thiazol-4-yl)acetyl]amino]-3-[(3-methyl-1,2,4-thiadiazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateYield 31.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Stannous chloride dihydrate (84.6 mg) was added to a solution of 1-ethoxycarbonyloxyethyl 7-[(Z)-2-methoxyimino-2-(thiazol-4-yl)acetamido]-3-(3-methyl-1,2,4-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylate-1-oxide (96.6 mg) in dimethylformamide (2 ml), and then acetyl chloride (0.38 ml) was added dropwise to the mixture with stirring while cooling with ice. After further stirring in 20° C. for 15 min, the reaction mixture was poured into a mixture of water (20 ml) and ethyl acetate (15 ml). The ethyl acetate layer was separated and the aqueous layer was extracted twice with ethyl acetate (15 ml). The whole ethyl acetate layer combined was dried over MgSO4, concentrated in vacuo, and the residue was added to petroleum ether (30 ml). The resulting crystals were filtered, washed with petroleum ether, and dried in vacuo to give the title compound (30 mg). ##STR24##

Workup

  1. temperaturewhile cooling with ice
  2. stirringAfter further stirring in 20° C. for 15 min
  3. customThe ethyl acetate layer was separated
  4. extractionthe aqueous layer was extracted twice with ethyl acetate (15 ml)
  5. dry with materialThe whole ethyl acetate layer combined was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. additionthe residue was added to petroleum ether (30 ml)
  8. filtrationThe resulting crystals were filtered
  9. washwashed with petroleum ether
  10. customdried in vacuo

Sources & evidence

ORD record
ord-89c48fd75ba14b9584b20001fdcbdaa4
Source dataset
uspto-grants-1988_08
Patent number
US04761409

Reaction notes

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