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

HRID 1421807노트

반응식

HRID 1421807 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-(tetrahydro-furan-2-yl)ceph-3-em-4-carboxylic acid (0.303 g, 0.78 mmol) (obtained in Example 12) in N-methylpyrrolidinone (5 ml) was added potassium carbonate (0.37 g, 2.66 mmol). Bromomethyl acetate (0.30 g, 1.95 mmol) was added dropwise to the mixture over 1 h. The mixture was stirred for a further 1 h, 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 (0.198 g, 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 18.9 Hz), 3.59 (1H, d), 3.65 (2H, ABq, J 16.4 Hz), 3.88 (2H, m), 4.89 (1H, dd, J 9.0, 6.7 Hz), 4.93 (1H, d, J 4.9 Hz), 5.84 (3H, m), 6.01 (1H, d, 9.1 Hz) 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-dc55f1ab7e1341ff9b8de61d7abb1469
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06077952

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