Hydrochloric Acid → 4-Carboxybutyl 5-amino-4-oxopentanoate hydrochloride

HRID 1771042Notes

Reaction equation

HRID 1771042 reaction equation
C([NH:11][CH2:12][C:13](=[O:33])[CH2:14][CH2:15][C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25]CC1C=CC=CC=1)=[O:24])=[O:17])(OCC1C=CC=CC=1)=O.[ClH:34]>[Pd].CC(O)C>[ClH:34].[NH2:11][CH2:12][C:13](=[O:33])[CH2:14][CH2:15][C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[O:17]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 900345714-(benzyloxycarbonyl)butyl 5-(Cbz-amino)-4-oxopentanoate

Product 1

HCID 900345074-Carboxybutyl 5-amino-4-oxopentanoate hydrochlorideYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

A stirred mixture of the product from 8c (0.70 g; 1.54 mmol), 12 M HCl (0.13 mL; 1.54 mmol), 10% Pd/C (Degussa type E101 NE/W) (100 mg), and 2-propanol (25 mL) was hydrogenated at ambient temperature and 4 bars pressure overnight. The mixture was filtered through a Celite® 545 pad; the filtrate was evaporated and the residue was triturated with dry diethyl ether (3×5 mL). After drying of the residue at ambient temperature and 0.01 mm Hg, 0.38 g (97%) product was obtained (white solid).

Workup

  1. customwas hydrogenated at ambient temperature
  2. custom4 bars pressure overnight
  3. filtrationThe mixture was filtered through a Celite® 545 pad
  4. customthe filtrate was evaporated
  5. customthe residue was triturated with dry diethyl ether (3×5 mL)
  6. customAfter drying of the residue at ambient temperature

Sources & evidence

ORD record
ord-7d2763d0649b4e1d82c3be28bba587e6
Source dataset
uspto-grants-2016_02
Patent number
US09249086B2

Reaction notes

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