2-Dimethylaminopyridine → 2',3'-Difluoro-4'-(4-pentyloxybutoxy)-biphenyl-4-carboxylic acid 4-[(R)-1-trifluoromethylheptyloxycarbonyl]-phenyl ester

HRID 6599

반응식

HRID 6599 반응식
[CH2:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([OH:25])=[O:24])=[CH:19][CH:18]=2)=[C:13]([F:26])[C:12]=1[F:27])[CH2:2][CH2:3][CH3:4].C(O[C:36]1[CH:55]=[CH:54][C:39]([C:40]([O:42][C@@H:43]([C:50]([F:53])([F:52])[F:51])[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])=[O:41])=[CH:38][CH:37]=1)C1C=CC=CC=1.[CH3:56]N(C1C=CC=CN=1)C>C1COCC1.C(N=C=NC(C)C)(C)C>[F:51][C:50]([F:52])([F:53])[C@H:43]([O:42][C:40]([C:39]1[CH:38]=[CH:37][C:36]([O:24][C:23]([C:20]2[CH:19]=[CH:18][C:17]([C:14]3[CH:15]=[CH:16][C:11]([O:10][CH2:9][CH2:8][CH2:7][CH2:6][O:5][CH2:1][CH2:2][CH2:3][CH2:4][CH3:56])=[C:12]([F:27])[C:13]=3[F:26])=[CH:22][CH:21]=2)=[O:25])=[CH:55][CH:54]=1)=[O:41])[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49]

참가 물질

6

반응물 3

HCID 218852-DimethylaminopyridineHCID 220162534'-(4-Butoxybutoxy)-2',3'-difluorobiphenyl-4-carboxylic acidHCID 22850730(R)-(+)-1,1,1-trifluoro-2-octyl 4-benzyloxybenzoate

생성물 1

HCID 586796342',3'-Difluoro-4'-(4-pentyloxybutoxy)-biphenyl-4-carboxylic acid 4-[(R)-1-trifluoromethylheptyloxycarbonyl]-phenyl ester수율 65%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 12734Diisopropylcarbodiimide용매

실험 절차

To a solution of 4′-(4-butoxybutoxy)-2′,3′-difluorobiphenyl-4-carboxylic acid (27) (1 equi.), (4-hydroxybenzoic acid (R)-1-trifluoromethyl-heptyl ester (13, Scheme 7) (1 equi.), and DMAP (dimethylaminopyridine) (0.1 equi.) in THF (25 mL/mmole), DIC (diisopropyl carbodiimide) (1.2 equi.) was added at room temperature. The reaction mixture was stirred at that temperature for 24 h, quenched with water, extracted with ethyl acetate:hexane(1:1), washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (5% EtOAc/hexanes) gave 2′,3′-difluoro-4′-(4-pentyloxybutoxy)-biphenyl-4-carboxylic acid 4-[(R)-1-trifluoromethylheptyloxycarbonyl]-phenyl ester (28) as a white solid (65%).

후처리

  1. customquenched with water
  2. extractionextracted with ethyl acetate:hexane(1:1)
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography on silica gel (5% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-66e871d4bd824865a6d3a12ea3da7ade
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07083832B2

연결된 노트

불러오는 중…