(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 1039027Notes

Reaction equation

HRID 1039027 reaction equation
[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]

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-5d14e30e998d4ccab349a3cbfe997782
Source dataset
uspto-grants-2013_10
Patent number
US08552032B2

Reaction notes

Loading…