HCID 86699355, compound → HCID 86699354, compound

HRID 333991Notes

Reaction equation

HRID 333991 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:9][C@H:10]([NH:12]C(=O)OCC1C=CC=CC=1)[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[C].[Pd]>[NH2:12][C@H:10]([CH3:11])[CH2:9][N:8]([CH2:23][CH2:24][CH2:25][CH3:26])[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 86699355HCID 86699355, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86699354HCID 86699354, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A suspension of 300 mg of (R)-benzyl 1-{tert-butoxycarbonyl(butyl)amino}propan-2-ylcarbamate and 30 mg of 10% palladium-carbon in 10 mL of methanol was vigorously stirred at room temperature for 16 hours in a hydrogen gas atmosphere. The reaction solution was filtered through celite, and the filtrate was concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (dichloromethane:methanol=10:1) to obtain 180 mg of the title compound as a colorless oil (95%).

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained crude product
  4. customwas purified by silica gel column chromatography (dichloromethane:methanol=10:1)

Sources & evidence

ORD record
ord-d25f951d62794f9d8f7c4542827e936e
Source dataset
uspto-grants-2014_11
Patent number
US08883792B2

Reaction notes

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