Triphenylphosphine → (S)-2-{2-methyl-4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-3-phenyl-propionic acid benzyl ester

HRID 1452698노트

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HRID 1452698 반응식
[CH2:1]([O:8][C:9](=[O:19])[C@H:10]([OH:18])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][C:21]1[CH:26]=[C:25]([C:27]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=2)([C:32]([F:35])([F:34])[F:33])[C:28]([F:31])([F:30])[F:29])[CH:24]=[CH:23][C:22]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH2:1]([O:8][C:9](=[O:19])[C@@H:10]([O:18][C:22]1[CH:23]=[CH:24][C:25]([C:27]([O:36][CH2:37][C:38]2[CH:39]=[CH:40][C:41]([O:44][CH3:45])=[CH:42][CH:43]=2)([C:28]([F:31])([F:30])[F:29])[C:32]([F:33])([F:34])[F:35])=[CH:26][C:21]=1[CH3:20])[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 9992574Benzyl (R)-(+)-2-hydroxy-3-phenylpropionateHCID 866042292-Methyl-4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenol

생성물 1

HCID 86604228(S)-2-{2-methyl-4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-3-phenyl-propionic acid benzyl ester수율 71%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To 1.27 g (4.9 mmol) of (R)-2-hydroxy-3-phenyl-propionic acid benzyl ester in 10 mL of THF were added 1.5 g (3.8 mmol) of 2-methyl-4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenol (example 2) and 1.3 g (4.9 mmol) of triphenylphosphine. The mixture was cooled to 0° C., treated with 0.77 mL (4.9 mmol) of DEAD and stirred at room temperature overnight. The solvent was evaporated and the crude mixture was purified by column chromatography on silica gel with EtOAc/n-heptane 1:4 to yield 1.7 g (71%) of (S)-2-{2-methyl-4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-3-phenyl-propionic acid benzyl ester as a light yellow oil, MS: 632 (M)+.

후처리

  1. customThe solvent was evaporated
  2. customthe crude mixture was purified by column chromatography on silica gel with EtOAc/n-heptane 1:4

출처 및 근거

ORD 기록
ord-17f700b2c860408290a9db94fa00f096
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07473705B2

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