HCID 71250018, compound → HCID 71245429, compound

HRID 1186014Notes

Reaction equation

HRID 1186014 reaction equation
C(OC(=O)[NH:10][C@@H:11]([CH2:35][OH:36])[C:12]([N:14]1[CH2:18][CH2:17][CH2:16][C@H:15]1[C:19]([N:21]1[CH2:25][CH2:24][CH2:23][C@H:22]1[C:26](=[O:34])[NH:27][C@@H:28]([CH2:32][OH:33])[C:29]([NH2:31])=[O:30])=[O:20])=[O:13])C1C=CC=CC=1>CO.[Pd]>[NH2:31][C:29](=[O:30])[C@@H:28]([NH:27][C:26]([C@@H:22]1[CH2:23][CH2:24][CH2:25][N:21]1[C:19]([C@@H:15]1[CH2:16][CH2:17][CH2:18][N:14]1[C:12](=[O:13])[C@@H:11]([NH2:10])[CH2:35][OH:36])=[O:20])=[O:34])[CH2:32][OH:33]

Participants

4

Reactant 1

HCID 71250018HCID 71250018, compound

Product 1

HCID 71245429HCID 71245429, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Benzyl-(S)-1-((S)-2-((S)-2-((S)-1-amino-3-hydroxy-1-oxopropan-2-ylcarbamoyl)pyrrolidine-1-carbonyl)pyrrolidin-1-yl)-3-hydroxy-1-oxopropan-2-ylcarbamate 7 (300 mg, 0.57 mmol) was dissolved in methanol (8 mL), 10% Pd/C (50 mg) was added and reaction mixture was stirred under hydrogen atmosphere for 2 h. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to yield compound C (150 mg, 68%).

Workup

  1. customreaction mixture
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7cb905158e4841b48ad5fbf7d1b77167
Source dataset
uspto-grants-2014_03
Patent number
US08673843B2

Reaction notes

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