4-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-3-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester → HCID 67410158, compound

HRID 1949633Notes

Reaction equation

HRID 1949633 reaction equation
C(OC([N:11]1[CH2:15][CH:14]([C:16]2[C:24]3[C:19](=[CH:20][C:21]([F:25])=[CH:22][CH:23]=3)[NH:18][CH:17]=2)[CH:13]2[N:26]([C:29](=[O:45])[CH:30]([NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)[CH2:27][CH2:28][CH:12]12)=O)C1C=CC=CC=1>CO>[C:41]([O:40][C:38](=[O:39])[NH:37][CH:30]([CH:31]1[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]1)[C:29]([N:26]1[CH2:27][CH2:28][CH:12]2[NH:11][CH2:15][CH:14]([C:16]3[C:24]4[C:19](=[CH:20][C:21]([F:25])=[CH:22][CH:23]=4)[NH:18][CH:17]=3)[CH:13]12)=[O:45])([CH3:44])([CH3:42])[CH3:43]

Participants

3

Reactant 1

HCID 674114834-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-3-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

Product 1

HCID 67410158HCID 67410158, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 500 mL Parr bottle was charged with crude 48 (1.5 g, 2.4 mmol) and 10% Pd-on-carbon (300 mg) in reagent grade MeOH (20 mL). The mixture was pressurized to 50 PSI H2 (344.7 KPa) then shaken for 2 h. The catalyst was removed by filtration through diatomaceous earth (Celite®) and the solids were washed with MeOH and EtOAc. The filtrate was concentrated in vacuo to afford 1.1 g of 49 which was used without further purification. 1H NMR (300 MHz, CDCl3): δ9.03 (s, 1H), 8.16 (dd, J=5.4 Hz, 8.4 Hz, 1H), 7.57 (s, 1H), 7.00 (d, J=8.7 Hz, 1H), 6.93 (t, J=8.7 Hz, 1H), 5.30 (d, J=8.7 Hz, 1H), 4.76 (m, 1H), 4.30-4.20 (m, 4H), 3.89 (m, 2H), 3.55 (m, 1H), 3.48 (s, 3H), 2.73-2.69 (m, 1H), 2.05-1.99 (m, 1H), 1.74-1.65 (m, 8H), 1.43 (s, 9H), 1.26-1.06 (m, 2H) ppm. Mass spectrum, m/z [485.3] (M+H)+.

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth (Celite®)
  2. washthe solids were washed with MeOH and EtOAc
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-552e7205c71a45d685e477d0f5769196
Source dataset
uspto-grants-2013_03
Patent number
US08399683B2

Reaction notes

Loading…