Quinine → (2S,3R)-2-(tert-butoxycarbonylamino)-3-hydroxy-3-(4-(trifluoromethyl)phenyl)propanoic acid

HRID 1425923노트

반응식

HRID 1425923 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH:13]([OH:24])[C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].COC1C=CC2N=CC=C([C@@H](O)[C@H]3N4C[C@H](C=C)[C@@H](CC4)C3)C=2C=1.CC1(C)O[C@]2(OC[C@@H]3OC(C)(C)O[C@@H]3C2=O)CO1>CCOCC>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@H:13]([OH:24])[C:14]1[CH:15]=[CH:16][C:17]([C:20]([F:22])([F:23])[F:21])=[CH:18][CH:19]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 3034034QuinineHCID 11391247L-enantiomerHCID 68281361(R)-2-(tert-butoxycarbonylamino)-3-hydroxy-3-(4-(trifluoromethyl)phenyl)propanoic acid

생성물 1

HCID 69283154(2S,3R)-2-(tert-butoxycarbonylamino)-3-hydroxy-3-(4-(trifluoromethyl)phenyl)propanoic acid수율 68%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

To a solution of (R)-2-(tert-butoxycarbonylamino)-3-hydroxy-3-(4-(trifluoromethyl)phenyl)propanoic acid (LXXVIII) (35 g, 100 mmol) in Et2O (600 mL) was added quinine (34 g, 100 mmol) in portions. The reaction was stirred at room temperature for 30 min at which time the white precipitate (L-enantiomer salt) was filtered and washed with Et2O. The solid was taken up in EtOAc/aqueous KHSO4. The organic layer was washed with aqueous KHSO4, brine and dried over MgSO4. The solvent was removed in vacuo to give optically pure (Marfey test) (2S,3R)-2-(tert-butoxycarbonylamino)-3-hydroxy-3-(4-(trifluoromethyl)phenyl)propanoic acid (LXXIX) (12 g, 34 mmol, 68% yield). 1H NMR (DMSO-d6) δ ppm 1.33 (s, 9H), 4.09 (brs, 1H), 5.13 (brs, 1H), 5.56 (brs, 1H), 7.47 (d, J=8 Hz, 2H), 7.56 (d, J=8 Hz, 2H); 19F NMR (DMSO-d6) δ ppm −60.15; ESIMS found for C15H18F3NO5 m/z 348 (M−H)

후처리

  1. filtrationwas filtered
  2. washwashed with Et2O
  3. washThe organic layer was washed with aqueous KHSO4, brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-569652b1339c4813b5c3ced59a6729c0
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933018B2

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