Tetrahydrofuran → (3S,4R)-3-((tert-butoxycarbonyl)amino)-4-((6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)amino)cyclopentane-1-carboxylic acid

HRID 56391노트

반응식

HRID 56391 반응식
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C@H:13]([NH:14][C:15]2[N:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:25]4[C:30]([Cl:31])=[C:29]([O:32][CH3:33])[CH:28]=[C:27]([O:34][CH3:35])[C:26]=4[Cl:36])[CH:21]=3)[N:16]=2)[CH2:12][CH:11]([C:37]([O:39]C)=[O:38])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1.[OH-].[Na+]>CO>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C@H:13]([NH:14][C:15]2[N:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:25]4[C:26]([Cl:36])=[C:27]([O:34][CH3:35])[CH:28]=[C:29]([O:32][CH3:33])[C:30]=4[Cl:31])[CH:21]=3)[N:16]=2)[CH2:12][CH:11]([C:37]([OH:39])=[O:38])[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 118036222Methyl (3S,4R)-3-((tert-butoxycarbonyl)amino)-4-((6-(2,6-dichloro-3,5-dimethoxyphenyl)-quinazolin-2-yl)amino)cyclopentane-1-carboxylate

생성물 1

HCID 118036129(3S,4R)-3-((tert-butoxycarbonyl)amino)-4-((6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)amino)cyclopentane-1-carboxylic acid수율 91%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Methyl (3S,4R)-3-((tert-butoxycarbonyl)amino)-4-((6-(2,6-dichloro-3,5-dimethoxyphenyl)-quinazolin-2-yl)amino)cyclopentane-1-carboxylate (0.662 g, 1.119 mmol) was taken up in methanol (10 ml), THF (4 ml) and treated with 10 ml of 1N NaOH. The reaction mixture was stirred at room temperature for 2 hours. The organic solvents were removed under reduced pressure, then the aqueous layer was acidified with 1N HCl to pH ˜2. The aqueous layer was extracted with EtOAcx3. The organic layers were combined, dried over sodium sulfate, and the solvent removed to give crude (3S,4R)-3-((tert-butoxycarbonyl)amino)-4-((6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)amino)cyclopentane-1-carboxylic acid (0.580 g, 1.00 mmol, 91% yield) which was carried on with further purification. MS (ES+) C27H30Cl2N4O6 requires: 577, found: 578 [M+H]+.

후처리

  1. customThe organic solvents were removed under reduced pressure
  2. extractionThe aqueous layer was extracted with EtOAcx3
  3. dry with materialdried over sodium sulfate
  4. customthe solvent removed

출처 및 근거

ORD 기록
ord-58ba660d6d7445e2b0dae34dcc86da6b
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434700B2

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