HCID 86699362, compound → HCID 86699361, compound

HRID 333996Notes

Reaction equation

HRID 333996 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:23][C@@H:24]([OH:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[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.[OH-].[Pd+2].[OH-].[C]>[NH2:12][C@H:10]([CH3:11])[CH2:9][N:8]([CH2:23][C@@H:24]([OH:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 86699362HCID 86699362, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86699361HCID 86699361, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 887MethanolSolvent

Procedure

2.85 g of (R)-benzyl 1-[tert-butoxycarbonyl{(S)-2-hydroxy-2-phenylethyl}amino]propan-2-ylcarbamate was dissolved in 40 mL of methanol. To the solution, 1.42 g of 20% palladium hydroxide-carbon was added, and the mixture was vigorously stirred at room temperature for 14 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=4:1) to obtain 1.86 g of the title compound as a colorless oil (96%).

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=4:1)

Sources & evidence

ORD record
ord-7af2f0dfcbf943eaa63bf43f8c9a82c8
Source dataset
uspto-grants-2014_11
Patent number
US08883792B2

Reaction notes

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