HCID 70273308, compound → HCID 54010657, compound

HRID 1598886Notes

Reaction equation

HRID 1598886 reaction equation
C(OC([NH:11][C@@H:12]([CH:33]([CH3:35])[CH3:34])[C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20]([NH:22][C@H:23]([C@@H:27]([OH:32])[C:28]([F:31])([F:30])[F:29])[CH:24]([CH3:26])[CH3:25])=[O:21])=[O:14])=O)C1C=CC=CC=1>C(O)C.[Pd]>[NH2:11][C@@H:12]([CH:33]([CH3:35])[CH3:34])[C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20]([NH:22][C@H:23]([C@@H:27]([OH:32])[C:28]([F:31])([F:29])[F:30])[CH:24]([CH3:26])[CH3:25])=[O:21])=[O:14]

Participants

4

Reactant 1

HCID 70273308HCID 70273308, compound

Product 1

HCID 54010657HCID 54010657, compoundYield 63.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of compound B (55 g) in ethanol (300 ml) was hydrogenated for 3 hours over 10% palladium on carbon catalyst (5.5 g), under a hydrogen pressure of 55 psi. The reaction mixture was filtered through diatomaceous earth and the filtrate was concentrated under vacuum to give a viscous oil. The oil was triturated with diethyl ether (250 ml) for 16 hours and the resulting solid was collected by filtration to give (S)-1-[(S)-2-amino-3-methylbutyryl]-N-[(S)-2-methyl-1-((R)-2,2,2-trifluoro-1-hydroxyethyl)propyl]pyrrolidine-2-carboxamide (C) (25.6 g) as a white solid; NMR (300 MHz, d6 -DMSO): 0.75-0.97 (m, 12H), 1.42 (s, 1H), 1.65-2.0 (m, 5H), 2.78, 3.20 (each d, total 1H), 3.45, 3.60 (each m, total 1H), 3.82 (m, 1H), 4.10 (m, 1H), 4.45, 4.57 (each m,total 1H), 6.45 (br d, 1H), 7.45, 7.60 (each d, total 1H).

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. concentrationthe filtrate was concentrated under vacuum
  3. customto give a viscous oil
  4. customThe oil was triturated with diethyl ether (250 ml) for 16 hours
  5. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-7bd0b82d685548699601467084963da9
Source dataset
uspto-grants-1998_04
Patent number
US05739157

Reaction notes

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