HCID 10523771, compound → HCID 10610377, compound

HRID 1599694Notes

Reaction equation

HRID 1599694 reaction equation
[C:1]([O:5][C:6](=[O:27])[CH2:7][C@@H:8]([O:25][CH3:26])[C@@H:9]([N:13](C(OCC1C=CC=CC=1)=O)[CH3:14])[CH:10]([CH3:12])[CH3:11])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:27])[CH2:7][C@@H:8]([O:25][CH3:26])[C@@H:9]([NH:13][CH3:14])[CH:10]([CH3:11])[CH3:12])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 1

HCID 10523771HCID 10523771, compound

Product 1

HCID 10610377HCID 10610377, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of t-butyl-(3R,4S)-4-(N-benzyloxycarbonyl-N-methylamino)-3-methoxy-5-methylhexanoate (3.855 g, 10.17 mmol) in 100 ml methanol was added 10% Pd/C (0.541 g) and the mixture was hydrogenated until completion of the deprotection (tlc control). The catalyst was removed by filtration and the filtrate concentrated in vacuo. The resulting amorphous solid (2.49 g) can be crystallized from ether by adding a solution of HCl in dioxane.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe resulting amorphous solid (2.49 g) can be crystallized from ether
  4. additionby adding a solution of HCl in dioxane

Sources & evidence

ORD record
ord-5cdcfe2bb8d543d0857903ec1cb375b0
Source dataset
uspto-grants-1998_04
Patent number
US05741892

Reaction notes

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