Ethyl Acetate → HCID 131716158, compound

HRID 704273Notes

Reaction equation

HRID 704273 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:32][O:33][CH2:34][CH:35]=[CH2:36])[C:8]([NH:10][CH:11]2[C:30](=[O:31])[N:13]3[C:14]([C:27]([OH:29])=[O:28])=[C:15]([S:18]/[CH:19]=[CH:20]\[C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:43]([O:46][CH:47](Br)[CH3:48])(=[O:45])[CH3:44].C(OCC)(=O)C>CN(C)C=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:32][O:33][CH2:34][CH:35]=[CH2:36])[C:8]([NH:10][CH:11]2[C:30](=[O:31])[N:13]3[C:14]([C:27]([O:29][CH:47]([O:46][C:43](=[O:45])[CH3:44])[CH3:48])=[O:28])=[C:15]([S:18]/[CH:19]=[CH:20]\[C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 111375051-Bromoethyl acetate2×HCID 131716159HCID 131716159, compound

Product 1

HCID 131716158HCID 131716158, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-[2-(2-aminothiazol-4-yl)-2-allyloxyiminoacetamido]-3-[(Z)-2-(3-pyridyl)vinylthio]-3-cephem-4-carboxylic acid (syn isomer)(1.0 g) in N,N-dimethylformamide (20 ml) was added cesium carbonate (0.31 g). The mixture was stirred for 20 minutes at room temperature, and 1-bromoethyl acetate (0.96 g) was added dropwise thereto at 0°-3° C. After the mixture was stirred for 40 minutes, 1-bromoethyl acetate (0.3 g) was added thereto. After stirring for 1 hour, reaction mixture was poured into ethyl acetate (120 ml) and the insoluble material was filtered off. The filtrate was washed with water (120 ml x 2), an aqueous solution of sodium bicarbonate (50 ml x 1) and a saturated aqueous solution of sodium chloride successively and dried over magnesium sulfate. The ethyl acetate was distilled off under reduced pressure, and the residue was pulverized with diisopropyl ether to give 1-acetoxyethyl 7-[2-(2 -aminothiazol-4-yl)-2-allyloxyiminoacetamido]-3-[(Z)-2-(3-pyridyl)vinylthio]-3-cephem-4-carboxylate (syn isomer) (0.27 g).

Workup

  1. customat 0°-3° C
  2. stirringAfter the mixture was stirred for 40 minutes
  3. stirringAfter stirring for 1 hour
  4. customreaction mixture
  5. filtrationthe insoluble material was filtered off
  6. washThe filtrate was washed with water (120 ml x 2)
  7. dry with materialan aqueous solution of sodium bicarbonate (50 ml x 1) and a saturated aqueous solution of sodium chloride successively and dried over magnesium sulfate
  8. distillationThe ethyl acetate was distilled off under reduced pressure

Sources & evidence

ORD record
ord-fd98f4e037ca46a78ce4af3a59213d2c
Source dataset
uspto-grants-1991_01
Patent number
US04985555

Reaction notes

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