Hydrochloric Acid → HCID 10399143, compound

HRID 542645Notes

Reaction equation

HRID 542645 reaction equation
N#N.C(OC([NH:13][C@H:14]([C:22]([NH:24][CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[O:23])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=O)C1C=CC=CC=1.Cl>[Pd].C(O)C>[CH3:28][CH:27]([CH3:29])[CH2:26][CH2:25][NH:24][C:22](=[O:23])[C@H:14]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[NH2:13]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86741421HCID 86741421, compound

Product 1

HCID 10399143HCID 10399143, compoundYield 60.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of N2 -benzyloxycarbonyl-N-(3-methylbutyl)-L-phenylalaninamide (7.0 g.), ethanol (200 ml.) and palladium on carbon (10%, 250 mg.) was hydrogenated under pressure (40 p.s.i.g.) for three hours (10% uptake). Concentrated hydrochloric acid (1.65 ml.) was added and the hydrogenation was continued overnight. The mixture was filtered, and the filtrate was stripped of volatiles. A small amount of crystals separated from an ether-ethanol solution of the residue. The mother liquor was stripped of volatiles and purified by reverse phase high pressure liquid chromatography on octadecylsilated silica gel using ammonium acetate (0.2%) in methanol-water (65:35) as the eluant, affording N-(3-methylbutyl)-L-phenylalaninamide (2.5 g.) as a clear gum.

Workup

  1. waitthe hydrogenation was continued overnight
  2. filtrationThe mixture was filtered
  3. customA small amount of crystals separated from an ether-ethanol solution of the residue
  4. custompurified by reverse phase high pressure liquid chromatography on octadecylsilated silica gel

Sources & evidence

ORD record
ord-049532b7c120442280663cd07540c574
Source dataset
uspto-grants-1987_04
Patent number
US04658013

Reaction notes

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