HCID 54218676, 화합물 → HCID 54374078, 화합물

HRID 2287472노트

반응식

HRID 2287472 반응식
[C:1]([NH:9][C@@H:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([N+:19]([O-])=O)[CH:17]=2)[CH2:12][C@H:11]1[O:22][C:23](=[O:25])[CH3:24])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCOC(C)=O.O=[Pt]=O>[C:1]([NH:9][C@@H:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([NH2:19])[CH:17]=2)[CH2:12][C@H:11]1[O:22][C:23](=[O:25])[CH3:24])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 1

HCID 54218676HCID 54218676, 화합물

생성물 1

HCID 54374078HCID 54374078, 화합물

시약·촉매·용매 2

HCID 345198Adams' catalyst촉매HCID 8857Ethyl Acetate용매

실험 절차

A solution of trans-1-benzamido-2-acetoxy-6-nitroindane (one part), prepared as described in Preparation 2, in EtOAc is treated with H2 (60 psi) in the presence of PtO2 for several hours. The catalyst is removed and the solvent evaporated to give trans-1-benzamido-2-acetoxy-6-aminoindane. A solution of this aminoindane (1 part) in a mixture of pyridine (16 parts), 4-dimethylaminopyridine (0.15 parts), and CH2Cl2 is treated with a solution of an aroyl (RCOCl) chloride (1.2 parts) and the reaction stirred over night. The reaction is poured into ice-water, the organic layer separated and consecutively washed with saturated aqueous sodium bicarbonate and brine. The organics are dried and the solvent evaporated to give trans-1-benzamido-2-acetoxy-6-carboxamino-indane. A solution of this indane in 1 M NaOH in methanol was stirred over night. The reaction is poured into ice-water and extracted with CH2Cl2. The organic extracts are washed with brine, dried, and the solvent evaporated to give the trans-1-benzamido-2-hydroxy-6-carboxamnido-indane.

후처리

  1. customThe catalyst is removed
  2. customthe solvent evaporated

출처 및 근거

ORD 기록
ord-e59ec12a2d73433eaebe7484db79380d
출처 데이터셋
uspto-grants-2000_07
특허 번호
US06083986

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