Hydrochloride methanol → (S)-tert-Butyl 2-amino-3-((tert-butoxycarbonyl)amino)propanoate hydrochloride

HRID 2230213Notes

Reaction equation

HRID 2230213 reaction equation
C(OC([NH:11][C@@H:12]([CH2:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=O)C1C=CC=CC=1.CO.[ClH:31]>[Pd]>[ClH:31].[NH2:11][C@@H:12]([CH2:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:13]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:14]

Participants

4

Reactant 2

HCID 21893726Hydrochloride methanolHCID 53876012tert-Butyl (2S)-benzyloxycarbonylamino-3-tert-butoxycarbonylaminopropionate

Product 1

HCID 86585733(S)-tert-Butyl 2-amino-3-((tert-butoxycarbonyl)amino)propanoate hydrochlorideYield 99%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

13.1 g of tert-butyl (S)-2-benzyloxycarbonylamino-3-tert-butoxycarbonylaminopropionate were hydrogenated over 10% Pd/C in methanol/HCl. After 1.5 h, the mixture was filtered and the filtrate was concentrated in vacuo. 9.77 g (99%) of tert-butyl (S)-2-amino-3-tert-butoxycarbonylaminopropionate hydrochloride were obtained as a colorless solid.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5cd0063416f4469f846e0ad623b3f16c
Source dataset
uspto-grants-2002_07
Patent number
US06423712B1

Reaction notes

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