Sodium Bicarbonate → benzhydryl (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 247753ノート

反応式

HRID 247753 の反応式
Cl.[NH2:2][CH:3]1[C:30](=[O:31])[N:5]2[C:6]([C:14]([O:16][CH:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])=[C:7](/[CH:10]=[CH:11]\[CH2:12][CH3:13])[CH2:8][S:9][C@H:4]12.C([O-])(O)=O.[Na+].[NH2:37][C:38]1[S:39][CH:40]=[C:41](/[C:43](=[N:56]/[O:57][CH3:58])/[C:44](ON2C3C=CC=CC=3N=N2)=[O:45])[N:42]=1>C(OCC)(=O)C>[NH2:37][C:38]1[S:39][CH:40]=[C:41](/[C:43](=[N:56]/[O:57][CH3:58])/[C:44]([NH:2][CH:3]2[C:30](=[O:31])[N:5]3[C:6]([C:14]([O:16][CH:17]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[O:15])=[C:7](/[CH:10]=[CH:11]\[CH2:12][CH3:13])[CH2:8][S:9][C@H:4]23)=[O:45])[N:42]=1

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 102453094-{(1Z)-2-[(1H-Benzotriazol-1-yl)oxy]-N-methoxy-2-oxoethanimidoyl}-1,3-thiazol-2-amineHCID 70445679diphenylmethyl 7-amino-3-[(Z)-1-butenyl]-3-cephem-4-carboxylate hydrochloride

生成物 1

HCID 88669278benzhydryl (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収率 91%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

A suspension of diphenylmethyl 7-amino-3-[(Z)-1-butenyl]-3-cephem-4-carboxylate hydrochloride (1.41 g, 3.1 mmoles) in ethyl acetate (20 ml) was shaken with aqueous NaHCO3 to give a clear two-layer solution. The organic layer was separated, washed with water and then an aqueous saturated NaCl solution, and dried over MgSO4. To the dried filtrate was added 1-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetoxy]benzotriazole (1.27 g, 4.0 mmoles), and the mixture was stirred at room temperature for 20 hours. The reaction mixture was filtered and the filtrate was washed with aqueous NaHCO3, water and a saturated NaCl solution, dried over MgSO4 and evaporated in vacuo. The residue was chromatographed on a silica gel column (40 g) with 3:1 CHCl3 -ethyl acetate to yield 1.7 g (91%) of the title compound. TLC (silica gel): Rf 0.25 (1:1 CHCl3 -ethyl acetate).

後処理

  1. customto give a clear two-layer solution
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialan aqueous saturated NaCl solution, and dried over MgSO4
  5. filtrationThe reaction mixture was filtered
  6. washthe filtrate was washed with aqueous NaHCO3, water
  7. dry with materiala saturated NaCl solution, dried over MgSO4
  8. customevaporated in vacuo
  9. customThe residue was chromatographed on a silica gel column (40 g) with 3:1 CHCl3 -ethyl acetate

出典と根拠

ORDレコード
ord-846f15475dc248dda24962435a57061a
出典データセット
uspto-grants-1987_11
特許番号
US04708955

反応ノート

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