(S,E)-tert-butyl 3-(3-(2-(tert-butoxycarbonylamino)butanamido)prop-1-enyl)-1H-indole-1-carboxylate → 3-[3-(2-(S)-tert-butoxycarbonylamino-butyrylamino)-propyl]-indole-1-carboxylic acid tert-butyl ester

HRID 1039027ノート

反応式

HRID 1039027 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:32][CH3:33])[C:10]([NH:12][CH2:13]/[CH:14]=[CH:15]/[C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:17]=1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)C>[C:28]([O:27][C:25]([N:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]([CH2:15][CH2:14][CH2:13][NH:12][C:10](=[O:11])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:32][CH3:33])=[CH:17]1)=[O:26])([CH3:31])([CH3:29])[CH3:30]

参加物

4

反応物 1

HCID 67235756(S,E)-tert-butyl 3-(3-(2-(tert-butoxycarbonylamino)butanamido)prop-1-enyl)-1H-indole-1-carboxylate

生成物 1

HCID 672353373-[3-(2-(S)-tert-butoxycarbonylamino-butyrylamino)-propyl]-indole-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A 250 mL Parr hydrogenation vessel was charged with (S,E)-tert-butyl 3-(3-(2-(tert-butoxycarbonylamino)butanamido)prop-1-enyl)-1H-indole-1-carboxylate (280 mg, 0.42 mmol), 10% palladium on carbon (34 mg), and ethanol (6.0 mL). The vessel was evacuated and filled with hydrogen. This was repeated two more times. The vessel was then filled with 50 psi hydrogen. After 24 h, the resulting solution was filtered through CELITE and the filtrate concentrated in vacuo to yield 3-[3-(2-(S)-tert-butoxycarbonylamino-butyrylamino)-propyl]indole-1-carboxylic acid tert-butyl ester. 1H NMR (300 MHz, CDCl3) δ 7.21-7.24 (m, 1H), 7.07-7.12 (m, 1H), 6.64-6.71 (m, 1H), 6.42-6.46 (m, 1H), 4.38-4.45 (m, 1H), 3.39-3.53 (m, 2H), 2.53 (t, J=6.8 Hz, 2H), 1.67-1.96 (m, 4H), and 0.88-0.93 (m, 3H).

後処理

  1. customThe vessel was evacuated
  2. additionfilled with hydrogen
  3. additionThe vessel was then filled with 50 psi hydrogen
  4. filtrationthe resulting solution was filtered through CELITE
  5. concentrationthe filtrate concentrated in vacuo

出典と根拠

ORDレコード
ord-5d14e30e998d4ccab349a3cbfe997782
出典データセット
uspto-grants-2013_10
特許番号
US08552032B2

反応ノート

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