Triacetoxyperiodinane → N-[(1,3-dimethyl-indole-2-cabonyl)valinyl]-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic Acid, tert-butyl Ester

HRID 634948노트

반응식

HRID 634948 반응식
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH3:11])=[C:3]1[C:12]([NH:14][C@H:15]([C:19]([NH:21][CH:22]([CH:31]([OH:44])[CH2:32][O:33][C:34]1[C:39]([F:40])=[C:38]([F:41])[CH:37]=[C:36]([F:42])[C:35]=1[F:43])[CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:20])[CH:16]([CH3:18])[CH3:17])=[O:13].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH3:11])=[C:3]1[C:12]([NH:14][C@H:15]([C:19]([NH:21][CH:22]([C:31](=[O:44])[CH2:32][O:33][C:34]1[C:39]([F:40])=[C:38]([F:41])[CH:37]=[C:36]([F:42])[C:35]=1[F:43])[CH2:23][C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])=[O:20])[CH:16]([CH3:18])[CH3:17])=[O:13]

참가 물질

4

반응물 2

HCID 159087TriacetoxyperiodinaneHCID 86756369N-[(1,3-dimethyl-indole-2-cabonyl)valinyl]-3-amino-4-hydroxy-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic Acid, tert-butyl Ester

생성물 1

HCID 86756370N-[(1,3-dimethyl-indole-2-cabonyl)valinyl]-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic Acid, tert-butyl Ester수율 65.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of N-[(1,3-dimethyl-indole-2-carbonyl)valinyl]-3-amino-4-hydroxy-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl ester (209 mg, 0.33 mmol) in CH2Cl2 (5.0 ml) was added Dess-Martin periodinane (181 mg, 0.43 mmol) and the solution stirred for 10 min. at room temperature. The reaction was quenched with Na2S2O4, diluted with EtOAc, washed with NaHCO3, and brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by chromatography (1:1 EtOAc/hexane) to give the titled product as a white solid (135 mg, 64%).

후처리

  1. customThe reaction was quenched with Na2S2O4
  2. additiondiluted with EtOAc
  3. washwashed with NaHCO3, and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by chromatography (1:1 EtOAc/hexane)

출처 및 근거

ORD 기록
ord-687658cc66f54866b73f7b7d851a61e1
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06184244B2

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