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 1452698ノート

反応式

HRID 1452698 の反応式
[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

参加物

6

反応物 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

生成物 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 ester収率 71%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-17f700b2c860408290a9db94fa00f096
出典データセット
uspto-grants-2009_01
特許番号
US07473705B2

反応ノート

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