Ethyl Acetate → Acetoxymethyl (6R,7R)-7-phenylacetamido-3-(tetrahydrofuran-2-yl)ceph-3-em-4-carboxylate

HRID 376582노트

반응식

HRID 376582 반응식
NC1S[CH:4]=[C:5](/[C:7](=N/OC)/[C:8]([NH:10][C@@H:11]2[C:34](=[O:35])[N:13]3[C:14]([C:23]([O:25]COC(=O)C(C)(C)C)=O)=[C:15]([C@H:18]4[CH2:22][CH2:21][CH2:20][O:19]4)[CH2:16][S:17][C@H:12]23)=[O:9])N=1.[C:39](=[O:42])([O-:41])[O-].[K+].[K+].[C:45]([O:48]CBr)(=O)[CH3:46].C(OCC)(=O)C.CN1[CH2:62][CH2:61][CH2:60][C:59]1=O>O>[C:5]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:34](=[O:35])[N:13]3[C:14]([C:23]([O:41][CH2:39][O:42][C:45](=[O:48])[CH3:46])=[O:25])=[C:15]([CH:18]4[CH2:22][CH2:21][CH2:20][O:19]4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:62]=[CH:61][CH:60]=[CH:59][CH:4]=1

참가 물질

7

반응물 5

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 68536Bromomethyl acetateHCID 882588472,2-dimethylpropanoyloxymethyl (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-[(2R)-oxolan-2-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

생성물 1

HCID 53945347Acetoxymethyl (6R,7R)-7-phenylacetamido-3-(tetrahydrofuran-2-yl)ceph-3-em-4-carboxylate

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a solution of (6R,7R)-7-phenylacetamido-3-(tetrahydrofuran-2-yl)ceph-3-em-4-carboxylic acid (0.303g, 0.78mmol) (obtained in Example 12) in N-methylpyrrolidinone (5ml) was added potassium carbonate (0.37g, 2.66mmol). Bromomethyl acetate (0.30g, 1.95mmol) was added dropwise to the mixture over 1h. The mixture was stirred for a further 1h, then ethyl acetate and water were added. The organic phase was washed with water, brine, dried (MgSO4) and evaporated. The residue was purified by chromatography to give the title compound as a mixture of diastereomers (0.198g, 56%); major diastereomer(S); δH (CDCl3) 1.59 (1H, m), 1.95 (2H, m), 2.12 (3H, s), 2.38 (1H, m), 3.28 (1H, d, J 18.9Hz), 3.59 (1H, d), 3.65 (2H, ABq, J 16.4Hz), 3.88 (2H, m), 4.89 (1H, dd, J 9.0, 6.7Hz), 4.93 (1H, d, J 4.9Hz), 5.84 (3H, m), 6.01 (1H, d, 9.1Hz) and 7.34 (5H, m).

후처리

  1. washThe organic phase was washed with water, brine
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by chromatography

출처 및 근거

ORD 기록
ord-afc65ce75ebb40ff828e3f7f1d658b7b
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06020329

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