HCID 66589964, compound → HCID 66997073, compound

HRID 2363635Notes

Reaction equation

HRID 2363635 reaction equation
C([N:8]1[CH2:12][C@@H:11]2[C@@H:13]([NH:16][C:17](=[O:32])[C@@H:18]([N:23]([CH3:31])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:14][CH2:15][C@@H:10]2[CH2:9]1)C1C=CC=CC=1>C(O)C>[CH3:31][N:23]([C@@H:18]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:17]([NH:16][C@@H:13]1[C@@H:11]2[C@@H:10]([CH2:9][NH:8][CH2:12]2)[CH2:15][CH2:14]1)=[O:32])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27]

Participants

3

Reactant 1

HCID 66589964HCID 66589964, compound

Product 1

HCID 66997073HCID 66997073, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

tert-Butyl(S)-1-((3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-ylamino)-4-methyl-1-oxopentan-2-yl(methyl)carbamate (0.833 g, 1.878 mmol) from Example 222 and ethanol (10 mL) were added to 20% Pd(OH)2—C, wet (0.167 g, 1.186 mmol) in a 50 mL pressure bottle and stirred for 4 hours at 30 psi and ambient temperature. The mixture was filtered through a nylon membrane and the solvent was removed in vacuo to give tert-butyl methyl((S)-4-methyl-1-((3aR,4S,6aS)-octahydrocyclopenta[c]pyrrol-4-ylamino)-1-oxopentan-2-yl)carbamate: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.36-8.23 (m, 1H), 5.20-5.12 (m, 1H), 4.33-4.25 (m, 1H), 3.14-3.03 (m, 4H), 2.96-2.88 (m, 1H), 2.79 (ddd, J=12.7, 8.0, 2.0 Hz, 1H), 2.63-2.55 (m, 1H), 2.52-2.42 (m, 2H), 2.06-1.89 (m, 2H), 1.89-1.79 (m, 3H), 1.64-1.53 (m, 2H), 1.47 (s, 9H), 1.29-1.20 (m, 1H), 0.92-0.83 (m, 6H); MS (ESI+) m/z 354 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a nylon membrane
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f048a5531df84117bfb7cfcb8177de4e
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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