Hydrochloric Acid → 2-[2-Amino-2-(3-bromo-phenyl)-propoxy]-3,3,3-trifluoro-2-methyl-propionic acid methyl ester

HRID 81565

반응식

HRID 81565 반응식
[CH3:1][O:2][C:3](=[O:24])[C:4]([O:10][CH2:11][C:12]([N:21]=[N+]=[N-])([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Br:20])[CH:15]=1)[CH3:13])([CH3:9])[C:5]([F:8])([F:7])[F:6].[In].Cl.C([O-])([O-])=O.[K+].[K+]>C1COCC1.O>[CH3:1][O:2][C:3](=[O:24])[C:4]([O:10][CH2:11][C:12]([NH2:21])([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Br:20])[CH:15]=1)[CH3:13])([CH3:9])[C:5]([F:8])([F:7])[F:6]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 5359967IndiumHCID 866502592-[2-Azido-2-(3-bromo-phenyl)-propoxy]-3,3,3-trifluoro-2-methyl-propionic acid methyl ester

생성물 1

HCID 666656742-[2-Amino-2-(3-bromo-phenyl)-propoxy]-3,3,3-trifluoro-2-methyl-propionic acid methyl ester

시약·촉매·용매 1

HCID 21881883Oxolane--water (1/1)용매

반응 조건

온도
25 °C

실험 절차

To a solution of the 2-[2-azido-2-(3-bromo-phenyl)-propoxy]-3,3,3-trifluoro-2-methyl-propionic acid methyl ester (4.2 g, 9.22 mmol) in THF-H2O 3:1 (48 ml) was added indium (2.116 g, 18.43 mmol) followed by 4N aqueous HCl over a period of 20 min and stirring for 1 h at 25° C. The reaction mixture was added to a 10% aqueous K2CO3 solution and the product was extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered and evaporated. The crude product was purified by flash-chromatography on NEt3 deactivated silica gel (hexane/EtOAc 2:1 to EtOAc) to provide a diastereomeric mixture of the title compound as a yellow oil: TLC (EtOAc): Rf=0.46; HPLC RtH55=0.999 min; 1H NMR (360 MHz, CDCl3): δ 7.73 (s, 1H), 7.47 (d, 1H), 7.41 (d, 1H), 7.24 (t, 1H), 3.84 and 3.83 (s, 3H), 3.59 (s, 2H), 1.61 and 1.59 (s, 3H), 1.52 and 1.51 (s, 3H); ESIMS: 384, 386 [(M+H)+].

후처리

  1. extractionthe product was extracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by flash-chromatography on NEt3 deactivated silica gel (hexane/EtOAc 2:1 to EtOAc)
  7. customto provide

출처 및 근거

ORD 기록
ord-3cb9056988fb4cb18b883481526b6c27
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846658B2

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