HCID 68494557, compound → HCID 76677219, compound

HRID 1968428Notes

Reaction equation

HRID 1968428 reaction equation
C(OC(=O)[NH:10][CH:11]([C:16]([N:18]1[CH:26]2[CH:21]([CH2:22][CH2:23][CH2:24][CH2:25]2)[CH2:20][CH:19]1[C:27](=[O:41])[NH:28][CH:29]([CH:33]([C:35](=[O:40])[NH:36][CH:37]1[CH2:39][CH2:38]1)[OH:34])[CH2:30][CH2:31][CH3:32])=[O:17])[C:12]([CH3:15])([CH3:14])[CH3:13])C1C=CC=CC=1.[H][H]>CCO.[Pd]>[CH:37]1([NH:36][C:35]([CH:33]([OH:34])[CH:29]([NH:28][C:27]([CH:19]2[CH2:20][CH:21]3[CH:26]([CH2:25][CH2:24][CH2:23][CH2:22]3)[N:18]2[C:16](=[O:17])[CH:11]([NH2:10])[C:12]([CH3:14])([CH3:13])[CH3:15])=[O:41])[CH2:30][CH2:31][CH3:32])=[O:40])[CH2:38][CH2:39]1

Participants

5

Reactant 2

HCID 68494557HCID 68494557, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 76677219HCID 76677219, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Amide 93 (10.10 g, 1.0 eq) in EtOH (10 mL) was treated with 10% Pd/C (100 mg) and hydrogen gas was bubbled into the black suspension until starting material was consumed (monitored by TLC). Catalyst was removed by filtration and the filtrate concentrated in vacuo to give 852 mg (100% yield) of 1-(2-amino-3,3-dimethyl-butyryl)-octahydro-indole-2-carboxylic acid [1-(cyclopropylcarbamoyl-hydroxy-methyl)-butyl]-amide 94 as a white solid with consistent NMR data. 1H NMR (CDCl3) δ 4.40 (m, 1H), 4.20 (m, 1H), 4.10 (d, 1H), 3.95 (m, 1H), 2.70 (m, 1H), 2.40 (m, 2H), 2.0 (m, 2H), 1.60-1.80 (m, 6H), 1.50 (m, 2H), 1.30 (m, 3H), 1.20 (m, 1H), 1.00 (s, 9H), 0.90 (m, 3H), 0.75 (m, 2H), 0.55 (m, 2H)ppm.

Workup

  1. customwas bubbled into the black suspension
  2. customwas consumed (monitored by TLC)
  3. customCatalyst was removed by filtration
  4. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-e783fc2734a04c25a3cda4dc4b6193ff
Source dataset
uspto-grants-2013_04
Patent number
US08426359B2

Reaction notes

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