Potassium Carbonate → acetyloxymethyl (6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(Z)-but-1-enyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 247759

반응식

HRID 247759 반응식
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:27]/[O:28][CH3:29])/[C:8]([NH:10][CH:11]2[C:25](=[O:26])[N:13]3[C:14]([C:22]([OH:24])=[O:23])=[C:15](/[CH:18]=[CH:19]\[CH2:20][CH3:21])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.C([O-])([O-])=O.[K+].[K+].[C:36]([O:39][CH2:40]Br)(=[O:38])[CH3:37]>CN(C=O)C.C(OCC)(=O)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:27]/[O:28][CH3:29])/[C:8]([NH:10][CH:11]2[C:25](=[O:26])[N:13]3[C:14]([C:22]([O:24][CH2:40][O:39][C:36](=[O:38])[CH3:37])=[O:23])=[C:15](/[CH:18]=[CH:19]\[CH2:20][CH3:21])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 68536Bromomethyl acetate2회HCID 88669631(6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(Z)-but-1-enyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

생성물 1

HCID 88669099acetyloxymethyl (6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(Z)-but-1-enyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate수율 27.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매3회HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

To a mixture of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-[(Z)-1-butenyl]-3-cephem-4-carboxylic acid (300 mg, 0.69 m mole) and K2CO3 (95 mg, 0.69 m mole) in dry DMF (3 ml) was added dropwise at 0° C. a solution of bromomethyl acetate (105 mg, 0.69 m mole) in dry DMF (0.25 ml) and the mixture was stirred at 0° C. for 15 minutes. To the mixture was added again a solution of bromomethyl acetate (105 mg, 0.69 m mole) in dry DMF (0.25 ml). The reaction mixture was stirred for another 30 minutes and diluted with ethyl acetate (20 ml). The dilute was washed with water and a saturated NaCl solution, dried over anhydrous Na2SO4 and evaporated to dryness. The residue was dissolved in methanol and passed through a column of the packing (40 ml) of a PrepPAK cartridge (Waters), which was washed with water and then eluted with 50% methanol. The eluate was monitored by HPLC. The desired fractions were collected and evaporated to give 96 mg (27%) of the title compound. Estimated purity 90% (by HPLC). M.p. 149°-152° C.

후처리

  1. stirringThe reaction mixture was stirred for another 30 minutes
  2. washThe dilute was washed with water
  3. dry with materiala saturated NaCl solution, dried over anhydrous Na2SO4
  4. customevaporated to dryness
  5. dissolutionThe residue was dissolved in methanol
  6. washwas washed with water
  7. washeluted with 50% methanol
  8. customThe desired fractions were collected
  9. customevaporated

출처 및 근거

ORD 기록
ord-20e2f20557624d10b2a7cb896fae76fc
출처 데이터셋
uspto-grants-1987_11
특허 번호
US04708955

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