Hydrochloric Acid → {[2-Fluoro-4-(4-fluoro-benzyloxy)-phenylcarbamoyl]-methyl}-carbamic acid tert-butyl ester

HRID 1884163노트

반응식

HRID 1884163 반응식
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[NH2:17].Cl.[C:19]([NH:26][CH2:27][C:28](O)=[O:29])([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C1(N=C=NC2CCCCC2)CCCCC1.N1C=CC=CC=1.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[C:22]([O:21][C:19](=[O:20])[NH:26][CH2:27][C:28](=[O:29])[NH:17][C:3]1[CH:4]=[CH:5][C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[CH:7][C:2]=1[F:1])([CH3:25])([CH3:23])[CH3:24]

참가 물질

8

반응물 6

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 516892Sodium BicarbonateHCID 221378852-Fluoro-4-(4-fluoro-benzyloxy)-phenylamine

생성물 1

HCID 69010933{[2-Fluoro-4-(4-fluoro-benzyloxy)-phenylcarbamoyl]-methyl}-carbamic acid tert-butyl ester수율 46%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 2-fluoro-4-(4-fluoro-benzyloxy)-phenylamine (1:1) hydrochloride (272 mg, 1 mmol), Boc-glycine (263 mg, 1.5 mmol), N,N′-dicylcohexylcarbodiimide (206 mg, 1 mmol) and pyridine (127 mg, 1.6 mmol) in ethyl acetate (6 mL) was stirred at room temperature for 3 h. After this time, the reaction mixture wa poured into sodium hydrogen carbonate (saturated), and the mixture extracted with ethyl acetate. The combined organic layers were then washed with brine and dried. Filtration and evaporation afforded the title compound (180 mg, 46%) as a light brown solid after chromatography on silica gel eluting with ethyl acetate: heptane (1:1 to 4:1). MS: m/e=393.1 (M++H).

후처리

  1. extractionthe mixture extracted with ethyl acetate
  2. washThe combined organic layers were then washed with brine
  3. customdried
  4. filtrationFiltration and evaporation

출처 및 근거

ORD 기록
ord-0cbb6872817948b88f05a0cb3249ad60
출처 데이터셋
uspto-grants-2004_07
특허 번호
US06762320B2

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