N-(tert-butoxycarbonyl)-L-aspartic acid 1-benzyl ester 4-piperidinamide → N-(tert-butoxycarbonyl)-L-aspartic acid 4-piperidinamide

HRID 1018463Notes

Reaction equation

HRID 1018463 reaction equation
C([O:8][C:9](=[O:23])[C@H:10]([CH2:19][C:20]([OH:22])=[O:21])[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])C1C=CC=CC=1.[NH:24]1[CH2:29][CH2:28][CH:27]([C:30]([NH2:32])=[O:31])[CH2:26][CH2:25]1.[H][H]>C(O)C.[Pd]>[NH:24]1[CH2:29][CH2:28][CH:27]([C:30]([NH2:32])=[O:31])[CH2:26][CH2:25]1.[C:15]([O:14][C:12]([NH:11][C@H:10]([C:9]([OH:23])=[O:8])[CH2:19][C:20]([OH:22])=[O:21])=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 2

HCID 70086528N-(tert-butoxycarbonyl)-L-aspartic acid 1-benzyl ester 4-piperidinamideHCID 178418361HCID 178418361, compound

Product 1

HCID 70086804N-(tert-butoxycarbonyl)-L-aspartic acid 4-piperidinamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of the compound from step A above (700 mg) in ethanol (30 mL) was exposed to a hydrogen atmosphere in the presence of 10% Pd-C (70 mg) for 4 hr at room temperature. After filtration (Celite filter aid) and rotoevaporation, N-(tert-butoxycarbonyl)-L-aspartic acid 4-piperidinamide (500 mg) was obtained as a yellowish foam.

Workup

  1. filtrationAfter filtration (Celite filter aid) and rotoevaporation

Sources & evidence

ORD record
ord-5d71e31486be41f2a5bdc2ba1027a8f0
Source dataset
uspto-grants-2002_11
Patent number
US06482827B1

Reaction notes

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