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m-Chloroperbenzoic acid → (4-methoxyphenyl)methyl (5S,6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-5,8-dioxo-3-[(2S)-oxolan-2-yl]-5lambda4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 376593
ノート
印刷プレビュー

反応式

HRID 376593 の反応式
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:37]/[O:38][CH3:39])/[C:8]([NH:10][C@@H:11]2[C:35](=[O:36])[N:13]3[C:14]([C:23]([O:25][CH2:26][C:27]4[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=4)=[O:24])=[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:6]=1.ClC1C=CC=C(C(OO)=[O:48])C=1>C(OCC)(=O)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:37]/[O:38][CH3:39])/[C:8]([NH:10][C@@H:11]2[C:35](=[O:36])[N:13]3[C:14]([C:23]([O:25][CH2:26][C:27]4[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=4)=[O:24])=[C:15]([C@@H:18]4[CH2:22][CH2:21][CH2:20][O:19]4)[CH2:16][S@:17](=[O:48])[C@H:12]23)=[O:9])[N:6]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 141582268(4-methoxyphenyl)methyl (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-[(2S)-oxolan-2-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

生成物 1

HCID 141582267(4-methoxyphenyl)methyl (5S,6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-5,8-dioxo-3-[(2S)-oxolan-2-yl]-5lambda4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate収率 69%

試薬・触媒・溶媒 1

HCID 8857
Ethyl Acetate
溶媒
2 回

実験手順

4-Methoxybenzyl (6R,7R)-7-[2-(2-aminothiazol-4-yl)-2-(Z)-methoxyiminoacetamido]-3-[(S)-tetrahydrofuran-2-yl]ceph-3-em-4-carboxylate (see example 7) (250mg, 0.44mmol) in ethyl acetate (25ml) was stirred in an ice bath and a solution of m-chloroperbenzoic acid (75mg, 0.44mmol) in ethyl acetate (5ml) was added. After 10 min the reaction mixture was washed with dilute aqueous sodium hydrogen carbonate then water followed by drying (magnesium sulphate) and evaporation under reduced pressure. The residue was chromatographed on silica gel eluting with acetone/ethyl acetate mixtures to give the title compound as a white solid (179mg, 69%); vmax (CHCl3) 1800, 1730, 1680 and 1610 cm-1 ; δH (CDCl3) 1.48-1.64 (1H,m), 1.89-2.00 (2H,m), 2.33-2.47 (1H,m), 3.29 and 3.75 (2H, ABq, J 19Hz), 3.82 (3H,s), 3.84-3.96 (2H,m), 4.09 (3H,s), 5.06 (1H,dd, J 7, 9Hz), 5.22 (2H,s), 5.55-5.8 (1H, br s, exch), 6.16 (1H,dd, J 4.5, 10Hz), 6.91 (2H,d, J 7,9Hz), 6.98 (1H,s), 7.35 (2H,d, J 9Hz) and 7.55-7.65 (1H,br, exch). [Mass spectrum: +ve ion (thioglycerol) MH+ (590)].

後処理

  1. washAfter 10 min the reaction mixture was washed with dilute aqueous sodium hydrogen carbonate
  2. customby drying
  3. custom(magnesium sulphate) and evaporation under reduced pressure
  4. customThe residue was chromatographed on silica gel eluting with acetone/ethyl acetate

出典と根拠

ORDレコード
ord-d32862e2cb3c468ba018a63787aa195f
出典データセット
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06020329

反応ノート

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