Water → (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (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 34266Notes

Reaction equation

HRID 34266 reaction equation
Br[CH2:2][C:3]1[O:4][C:5](=[O:9])[O:6][C:7]=1[CH3:8].[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(OCC)(=O)C.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][CH2:2][C:3]3[O:4][C:5](=[O:9])[O:6][C:7]=3[CH3:8])=[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 107741414-(Bromomethyl)-5-methyl-1,3-dioxol-2-oneHCID 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-carboxylate

Product 1

HCID 172980695(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (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 62.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Bromomethyl-5-methyl-1,3-dioxolene-2-one (386 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) at -5° C. The mixture was stirred at this temperature for 1.3 hr and then poured into a mixture of ethyl acetate (130 ml) and water (30 ml, adjusted to pH 3 with dil HCl) with stirring. The ethyl acetate layer was separated, washed successively with water (30 ml, adjusted to pH 3 with dil. HCl), 10% aqueous K2HPO4 solution (30 ml) twice, and saturated saline water, dried over MgSO4, concentrated in vacuo, and the residue was added dropwise to a mixture of diethyl ether (40 ml) and petroleum ether (40 ml). The formed crystals were filtered, washed with petroleum ether, and dried in vacuo to give the title compound (390 mg). ##STR38##

Workup

  1. stirringwith stirring
  2. customThe ethyl acetate layer was separated
  3. washwashed successively with water (30 ml, adjusted to pH 3 with dil. HCl), 10% aqueous K2HPO4 solution (30 ml) twice
  4. dry with materialsaturated saline water, dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. additionthe residue was added dropwise to a mixture of diethyl ether (40 ml) and petroleum ether (40 ml)
  7. filtrationThe formed crystals were filtered
  8. washwashed with petroleum ether
  9. customdried in vacuo

Sources & evidence

ORD record
ord-38d4a7355487418e87e2dbc91859906a
Source dataset
uspto-grants-1988_08
Patent number
US04761409

Reaction notes

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