Hydrochloric Acid → 1-(Isopropyl carboxy)ethyl 5-amino-4-oxopentanoate hydrochloride

HRID 1771027Notes

Reaction equation

HRID 1771027 reaction equation
C([NH:11][CH2:12][C:13](=[O:31])[CH2:14][CH2:15][C:16]([O:18][CH:19]([C:21]([O:23][CH2:24][C:25]1C=CC=CC=1)=[O:22])[CH3:20])=[O:17])(OCC1C=CC=CC=1)=O.[H][H].[ClH:34].[CH2:35](OCC)C>[Pd].CC(O)C.O1CCOCC1>[ClH:34].[NH2:11][CH2:12][C:13](=[O:31])[CH2:14][CH2:15][C:16]([O:18][CH:19]([C:21]([O:23][CH:24]([CH3:25])[CH3:35])=[O:22])[CH3:20])=[O:17]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 900344831-(benzyloxycarbonyl)ethyl 5-(Cbz-amino)-4-oxopentanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 900345551-(Isopropyl carboxy)ethyl 5-amino-4-oxopentanoate hydrochlorideYield 71%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A stirred mixture of the product of 2b (4.92 g; 11.5 mmol), 10% palladium on activated carbon (100 mg), hydrogen gas and 2.0 M hydrogen chloride in diethyl ether (10 mL; 20 mmol) in 2-propanol (15 mL) and dioxane (15 mL) was hydrogenated at ca. 6 bar for 2 days at ambient temperature. The mixture was filtered through a Celite® 545 pad and the residue was washed with 2-propanol (2×5 mL). The combined filtrates were evaporated and the resulting oil was triturated with diethyl ether (4×10 mL), then stored in a freezer. The oil did not solidify. After vacuum-drying (at 0.005 mm Hg) overnight, 1.97 g (71%) product was obtained (tan, viscous oil).

Workup

  1. filtrationThe mixture was filtered through a Celite® 545 pad
  2. washthe residue was washed with 2-propanol (2×5 mL)
  3. customThe combined filtrates were evaporated
  4. customthe resulting oil was triturated with diethyl ether (4×10 mL)
  5. customAfter vacuum-drying (at 0.005 mm Hg) overnight

Sources & evidence

ORD record
ord-c1834a4ed1b142c8a8af40fde901b6d5
Source dataset
uspto-grants-2016_02
Patent number
US09249086B2

Reaction notes

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