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

HRID 634955ノート

反応式

HRID 634955 の反応式
[C:1]([O:5][C:6]([CH2:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]1[C:18]([NH:20][C@H:21]([C:25]([NH:27][CH:28]([CH:37]([OH:50])[CH2:38][O:39][C:40]1[C:45]([F:46])=[C:44]([F:47])[CH:43]=[C:42]([F:48])[C:41]=1[F:49])[CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[O:26])[CH:22]([CH3:24])[CH3:23])=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]([O:5][C:6]([CH2:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]1[C:18]([NH:20][C@H:21]([C:25]([NH:27][CH:28]([C:37](=[O:50])[CH2:38][O:39][C:40]1[C:45]([F:46])=[C:44]([F:47])[CH:43]=[C:42]([F:48])[C:41]=1[F:49])[CH2:29][C:30]([O:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:31])=[O:26])[CH:22]([CH3:24])[CH3:23])=[O:19])=[O:7])([CH3:3])([CH3:4])[CH3:2]

参加物

4

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 86756375N-{[1-(tert-butyl)oxycarbonylmethyl-indole-2-cabonyl]valinyl}-3-amino-4-hydroxy-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl ester

生成物 1

HCID 86756376N-{[1-(tert-butyl)oxycarbonylmethyl-indole-2-cabonyl]valinyl}-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic Acid, tert-butyl Ester収率 82%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of N-{[1-(tert-butyl)oxycarbonylmethyl-indole-2-carbonyl]valinyl}-3-amino-4-hydroxy-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl ester (290 mg, 0-42 mmol) in CH2Cl2 (5.0 ml) was added Dess-Martin periodinane (204 mg, 0.48 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 (235 mg, 82%).

後処理

  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)

出典と根拠

ORDレコード
ord-5ac731f66e3240b28cfe008901320977
出典データセット
uspto-grants-2001_02
特許番号
US06184244B2

反応ノート

読み込み中…