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

HRID 376582ノート

反応式

HRID 376582 の反応式
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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-afc65ce75ebb40ff828e3f7f1d658b7b
出典データセット
uspto-grants-2000_02
特許番号
US06020329

反応ノート

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