Benzyl N-(tert-butoxycarbonyl)-4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)-L-phenylalaninate → (2S)-2-[(tert-butoxycarbonyl)amino]-3-[4-(2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]propanoic acid

HRID 724705ノート

反応式

HRID 724705 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:29]([O:31]CC1C=CC=CC=1)=[O:30])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[S:21](=[O:23])(=[O:22])[N:20]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:19](=[O:28])[CH:18]=2)=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[S:21](=[O:22])(=[O:23])[N:20]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:19](=[O:28])[CH2:18]2)=[CH:13][CH:12]=1)[C:29]([OH:31])=[O:30])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 1

HCID 11720867Benzyl N-(tert-butoxycarbonyl)-4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)-L-phenylalaninate

生成物 1

HCID 11568707(2S)-2-[(tert-butoxycarbonyl)amino]-3-[4-(2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]propanoic acid収率 65.1%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

To a solution of benzyl N-(tert-butoxycarbonyl)-4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)-L-phenylalaninate (1.3 g, 2.4 mmol) in ethanol (35 mL) in a parr shaker, palladium (0.700 g, 6.58 mmol) (Pd, 10% by weight on activated carbon) was added and hydrogenated overnight at 50 psi. The suspension was filtered through celite and concentrated to give the crude product. The crude was purified on preparative LCMS to give the product (0.71 g, 65%). LCMS found for C21H3N2O7S (M+H)+: m/z=455.

後処理

  1. filtrationThe suspension was filtered through celite and
  2. concentrationconcentrated
  3. customto give the crude product
  4. customThe crude was purified on preparative LCMS

出典と根拠

ORDレコード
ord-bc173ea7b91f4bc6a8a4c22ac6bedf82
出典データセット
uspto-grants-2006_11
特許番号
US07141596B2

反応ノート

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