Triphenylphosphine → (S)-2-[4-(5-Trifluoromethyl-pyridin-2-yloxy)-phenoxy]-propionic acid benzyl ester

HRID 239893

反応式

HRID 239893 の反応式
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[N:7][CH:8]=1.[CH2:19]([O:26][C:27](=[O:31])[C@H:28](O)[CH3:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH2:19]([O:26][C:27](=[O:31])[C@@H:28]([O:16][C:13]1[CH:12]=[CH:11][C:10]([O:9][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:17])[F:18])=[CH:8][N:7]=2)=[CH:15][CH:14]=1)[CH3:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 1552414-(5-Trifluoromethyl-pyridin-2-yloxy)-phenolHCID 5324736(R)-2-hydroxypropionic acid benzyl esterHCID 5363146Diisopropyl azodicarboxylate

生成物 1

HCID 67200117(S)-2-[4-(5-Trifluoromethyl-pyridin-2-yloxy)-phenoxy]-propionic acid benzyl ester収率 69%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4-(5-trifluoromethyl-pyridin-2-yloxy)-phenol (2.90 g, 11.4 mmol) and (R)-2-hydroxypropionic acid benzyl ester (2.25 g, 12.5 mmol) in dry THF (100 mls) at 0° C. under nitrogen is added triphenylphosphine followed by dropwise addition of diisopropylazodicarboxylate (3.36 mls, 17 mmol). The resulting yellow mixture is stirred for 1 hr then left the stand for 16 hours. The reaction mixture is partitioned between water and ethyl acetate and the layers separated. The aqueous is further extracted with ethyl acetate and the combined organic layers dried over magnesium sulphate, filtered and the solvent removed under reduced pressure. Column chromatography on silica gel using 10% ethyl acetate/hexane as eluent yielded (S)-2-[4-(5-Trifluoromethyl-pyridin-2-yloxy)-phenoxy]-propionic acid benzyl ester as a colourless oil. In one example 3.25 g are made representing 69% yield and in >99% ee (as determined by nmr).

後処理

  1. waitthen left the stand for 16 hours
  2. customThe reaction mixture is partitioned between water and ethyl acetate
  3. customthe layers separated
  4. extractionThe aqueous is further extracted with ethyl acetate
  5. dry with materialthe combined organic layers dried over magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

出典と根拠

ORDレコード
ord-f013d9db8b1b41f4bbdb7a3d43b97061
出典データセット
uspto-grants-2014_02
特許番号
US08642836B2

関連ノート

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