Benzoic Acid → (2R)-1-(Biphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol

HRID 1600905노트

반응식

HRID 1600905 반응식
N(C(OCC)=O)=NC(OCC)=O.[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][CH2:20][C@H:21]([OH:36])[CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:26][CH:25]=2)[CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)(=O)C1C=CC=CC=1>O1CCCC1>[C:27]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:26]=[CH:25][C:24]([O:23][CH2:22][C@H:21]([OH:36])[CH2:20][CH2:19][C:15]2[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=2)=[CH:29][CH:28]=1

참가 물질

6

반응물 4

HCID 243Benzoic AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 57091781(2S)-4-(3-Pyridyl)-1-[(4-phenyl)phenoxy]-butan-2-ol

생성물 1

HCID 54273256(2R)-1-(Biphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol수율 88%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Diethyl azodicarboxylate (0.123 ml) was added to a stirring solution of (2S)-4-(3-pyridyl)-1-[(4-phenyl)phenoxy]-butan-2-ol (0.25 g), triphenylphosphine (0.262 g) and benzoic acid (0.122 g) in tetrahydrofuran (10 ml) at 0° C. and the resulting solution was stirred for 1 hour. The mixture was concentrated under reduced pressure and the residue was redissolved in methanol (20 ml) and water (5 ml). Solid potassium hydroxide (0.112 g) was added and the reaction stirred for 2 hours before being poured into a solution of saturated aqueous sodium hydrogencarbonate. The mixture was extracted with ethyl acetate and the combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound (0.22 g) as a solid that was recrystallised from ethyl acetate:hexane.

후처리

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe residue was redissolved in methanol (20 ml)
  3. additionSolid potassium hydroxide (0.112 g) was added
  4. stirringthe reaction stirred for 2 hours
  5. additionbefore being poured into a solution of saturated aqueous sodium hydrogencarbonate
  6. extractionThe mixture was extracted with ethyl acetate
  7. dry with materialthe combined organic extracts were dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-2773b07186314449bde7ee5e1630e43a
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05977105

반응 노트

불러오는 중…