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 34264Notes

Reaction equation

HRID 34264 reaction equation
[C:1](=[O:9])([O-:8])[O:2][CH:3](C(Br)C)[CH3:4].[CH3:10][O:11]/[N:12]=[C:13](/[C:37]1[N:38]=[CH:39][S:40][CH:41]=1)\[C:14]([NH:16][CH:17]1[C:35](=[O:36])[N:19]2[C:20]([C:32]([O-:34])=[O:33])=[C:21]([CH2:24][S:25][C:26]3[S:30][N:29]=[C:28]([CH3:31])[N:27]=3)[CH2:22][S:23][C@H:18]12)=[O:15].[Na+].[C:43](OCC)(=O)[CH3:44].O>CN(C)C=O>[CH3:10][O:11]/[N:12]=[C:13](/[C:37]1[N:38]=[CH:39][S:40][CH:41]=1)\[C:14]([NH:16][CH:17]1[C:35](=[O:36])[N:19]2[C:20]([C:32]([O:34][CH:43]([O:8][C:1]([O:2][CH2:3][CH3:4])=[O:9])[CH3:44])=[O:33])=[C:21]([CH2:24][S:25][C:26]3[S:30][N:29]=[C:28]([CH3:31])[N:27]=3)[CH2:22][S:23][C@H:18]12)=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 88640724sodium (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-carboxylateHCID 131715658HCID 131715658, 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-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Bromoethylethyl carbonate (472 mg) was added to a solution of sodium 7-[(Z)-2-methoxyimino-2-(thiazol-4-yl)acetamido]-3-(3-methyl-1,2,4-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylate (536 mg) in dimethylformamide (5 ml) under cooling with ice. The mixture was stirred for 3 hr and then poured into a mixture of ethyl acetate (120 ml) and water (20 ml, adjusted to pH3 with dil. HCl) with stirring. The ethyl acetate layer was separated, washed successively with water (20 ml, adjusted to pH 3 with dil. HCl), 10% aqueous K2HPO4 solution (20 ml) twice, and saturated saline water (20 ml), drived over MgSO4, concentrated in vacuo, and the residue was added dropwise to petroleum ether. The formed crystals were filtered and dried in vacuo to give the title compound (325 mg). This product was found to contain the Δ2 isomer.

Workup

  1. temperatureunder cooling with ice
  2. stirringwith stirring
  3. customThe ethyl acetate layer was separated
  4. washwashed successively with water (20 ml, adjusted to pH 3 with dil. HCl), 10% aqueous K2HPO4 solution (20 ml) twice
  5. concentrationconcentrated in vacuo
  6. additionthe residue was added dropwise to petroleum ether
  7. filtrationThe formed crystals were filtered
  8. customdried in vacuo

Sources & evidence

ORD record
ord-cdf060f2be324d6095d78b4396236916
Source dataset
uspto-grants-1988_08
Patent number
US04761409

Reaction notes

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