Benzhydrylamine → benzhydryl (6R,7R)-3-methyl-8-oxo-7-[(2-phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 1657393

反応式

HRID 1657393 の反応式
[CH3:1][C:2]1[CH2:3][S:4][C@@H:5]2[C@H:12]([NH:13][C:14](=[O:23])[CH2:15][O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:11](=[O:24])[N:6]2[C:7]=1[C:8]([OH:10])=[O:9].[C:25]1([CH:31](N)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.N(OC(C)C)=O>C(#N)C>[CH3:1][C:2]1[CH2:3][S:4][C@@H:5]2[C@H:12]([NH:13][C:14](=[O:23])[CH2:15][O:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:11](=[O:24])[N:6]2[C:7]=1[C:8]([O:10][CH:31]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:9]

参加物

5

反応物 3

HCID 7036BenzhydrylamineHCID 10929Isopropyl nitriteHCID 111318273-Methyl-7beta-phenoxyacetamidoceph-3-em-4-carboxylic acid

生成物 1

HCID 112091benzhydryl (6R,7R)-3-methyl-8-oxo-7-[(2-phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

3-Methyl-7β-phenoxyacetamido ceph-3-em-4-carboxylic acid (3.48 g., 10 m. moles), diphenylmethylamine (3.20 g., 17.5 m. moles) and isopropyl nitrite (3.12 g., 35 m. moles) were heated at 35° over 2 hours in acetonitrile (50 ml). The solvent was removed in vacuo, replaced by ethyl acetate (50 ml) and washed as described in example 7. The organic residue was crystallised from hot isopropanol (30 ml) to yield the title ester (4.25 g., 82.6% based on the input acid) m.pt. 155°, pure by t.l.c.

後処理

  1. customThe solvent was removed in vacuo
  2. washwashed
  3. customThe organic residue was crystallised from hot isopropanol (30 ml)

出典と根拠

ORDレコード
ord-5c6aef9294b24b148c369dedfa9e2e54
出典データセット
uspto-grants-1976_06
特許番号
US03960843

関連ノート

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