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

반응식

HRID 1657393 반응식
[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]

참가 물질

5

반응물 3

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

생성물 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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-5c6aef9294b24b148c369dedfa9e2e54
출처 데이터셋
uspto-grants-1976_06
특허 번호
US03960843

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