Ethyl Acetate → HCID 131714963, compound

HRID 1731698Notes

Reaction equation

HRID 1731698 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:33][O:34][CH2:35][CH:36]=[CH2:37])[C:8]([NH:10][CH:11]2[C:31](=[O:32])[N:13]3[C:14]([C:28]([OH:30])=[O:29])=[C:15]([CH2:18][S:19]/[CH:20]=[CH:21]\[C:22]4[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:44]([O:47][CH:48](Br)[CH3:49])(=[O:46])[CH3:45].C(OCC)(=O)C>CN(C)C=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:33][O:34][CH2:35][CH:36]=[CH2:37])[C:8]([NH:10][CH:11]2[C:31](=[O:32])[N:13]3[C:14]([C:28]([O:30][CH:48]([O:47][C:44](=[O:46])[CH3:45])[CH3:49])=[O:29])=[C:15]([CH2:18][S:19]/[CH:20]=[CH:21]\[C:22]4[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=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 acetateHCID 131714964HCID 131714964, compound

Product 1

HCID 131714963HCID 131714963, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 7-[2-(2-aminothiazol-4-yl)-2-allyloxyiminoacetamido]-3-[(Z)-2-(3-pyridyl)vinylthiomethyl]-3-cephem-4-carboxylic acid (syn isomer) in N,N-dimethylformamide (30 ml) was added cesium carbonate (0.47 g). The mixture was stirred for 30 minutes at 25° C., and 1-bromoethyl acetate (1.35 g) was added dropwise thereto at 0°-3° C. After stirring for 1 hour, the reaction mixture was poured into ethyl acetate (200 ml) and the insoluble material was filtered off. The filtrate was washed with water (200 ml×2), an aqueous solution of sodium bicarbonate (100 ml×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)vinylthiomethyl]-3-cephem-4-carboxylate (syn isomer) (0.63 g).

Workup

  1. customat 0°-3° C
  2. stirringAfter stirring for 1 hour
  3. filtrationthe insoluble material was filtered off
  4. washThe filtrate was washed with water (200 ml×2)
  5. dry with materialan aqueous solution of sodium bicarbonate (100 ml×1) and a saturated aqueous solution of sodium chloride successively, and dried over magnesium sulfate
  6. distillationThe ethyl acetate was distilled off under reduced pressure

Sources & evidence

ORD record
ord-cfe418d590e9486ba444237e20f2c7cf
Source dataset
uspto-grants-1986_11
Patent number
US04622318

Reaction notes

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