HCID 70152428, compound → HCID 11299226, compound

HRID 1018715Notes

Reaction equation

HRID 1018715 reaction equation
C(O[CH2:9][NH:10][C@@H:11]([CH3:24])[C@H:12]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:13]([OH:15])=[O:14])C1C=CC=CC=1>CO.[Pd]>[CH3:9][NH:10][C@@H:11]([CH3:24])[C@H:12]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:13]([OH:15])=[O:14]

Participants

4

Reactant 1

HCID 70152428HCID 70152428, compound

Product 1

HCID 11299226HCID 11299226, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A solution of (2S,3S)-3-((benzyloxy)methylamino)-2-(tert-butoxyformamido)butyric acid 9 (2.4 g, 14.8 mmol) in 20 mL methanol was added under nitrogen to a suspension of 10% palladium on charcoal (0.6 g, 25 wt %) in 20 mL methanol in a Parr hydrogenator flask. The mixture was placed on the Parr hydrogenator and hydrogenated at 50 psi for 18 hours. The catalyst was removed by filtration and the filtrate evaporated in vacuo. The residue was then lyophilized, affording 1.55 g of (2S,3S)-3-methylamino-2-(tert-butoxyformamido)butyric acid 10 as a white solid (95% yield).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-9c59229670a6491883fe43194425bc3c
Source dataset
uspto-grants-2002_11
Patent number
US06482921B1

Reaction notes

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