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Sodium Carbonate → Benzhydryl 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido]-3-[2-(3-pyridyl)vinyl]-3-cephem-4-carboxylate

HRID 464220
ノート
印刷プレビュー

反応式

HRID 464220 の反応式
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[Cl-].[CH:10]([O:23][C:24]([C:26]1[N:31]2[C:32](=[O:48])[CH:33]([NH:34][C:35](=[O:47])[C:36]([C:41]3[N:45]=[C:44]([NH2:46])[S:43][N:42]=3)=[N:37][O:38][CH2:39][CH3:40])[C@H:30]2[S:29][CH2:28][C:27]=1[CH2:49][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:25])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O.C(OCC)(=O)C>[NH2:46][C:44]1[S:43][N:42]=[C:41]([C:36](=[N:37][O:38][CH2:39][CH3:40])[C:35]([NH:34][CH:33]2[C:32](=[O:48])[N:31]3[C:26]([C:24]([O:23][CH:10]([C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[O:25])=[C:27]([CH:49]=[CH:1][C:2]4[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=4)[CH2:28][S:29][C@H:30]23)=[O:47])[N:45]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 103713-PyridinecarboxaldehydeHCID 11430Potassium CarbonateHCID 131714367[4-Benzhydryloxycarbonyl-7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido]-3-cephem-3-ylmethyl]triphenylphosphonium chloride

生成物 1

HCID 131714369Benzhydryl 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido]-3-[2-(3-pyridyl)vinyl]-3-cephem-4-carboxylate
収率 48.1%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Nicotinaldehyde (1.1 g) was added to a solution of {4-benzhydryloxycarbonyl-7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido]-3-cephem-3-ylmethyl}triphenylphosphonium chloride (syn isomer) (3.0 g) in tetrahydrofuran (30 ml) and water (15 ml) and the solution was adjusted to pH 9.0 with 20% aqueous sodium carbonate. The solution was stirred at ambient temperature for 2 hours under keeping the pH 8.8 to 9.2 with 20% aqueous potassium carbonate. Ethyl acetate and water were added to the resulting solution. The separated organic layer was washed with saturated aqueous sodium chloride and dried over magnesium sulfate. The crude product obtained by concentration was purified by silica gel column chromatography using a mixture of acetone and dichloromethane (rate 1:1) as eluent. The eluted fractions were evaporated to give benzhydryl 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido]-3-[2-(3-pyridyl)vinyl]-3-cephem-4-carboxylate (syn isomer) (cis-trans mixture) (1.1 g).

後処理

  1. washThe separated organic layer was washed with saturated aqueous sodium chloride
  2. dry with materialdried over magnesium sulfate
  3. customThe crude product obtained by concentration
  4. customwas purified by silica gel column chromatography
  5. additiona mixture of acetone and dichloromethane (rate 1:1) as eluent
  6. customThe eluted fractions were evaporated

出典と根拠

ORDレコード
ord-9f082a8ffc664c818261c18cf156682a
出典データセット
uspto-grants-1985_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04546101

反応ノート

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