Hydrochloric Acid → methyl (2S)-2-[(2R)-2-aminopropanamido]-4-methylpentanoate hydrochloride

HRID 1763718Notes

Reaction equation

HRID 1763718 reaction equation
C(OC([NH:11][C@@H:12]([C:14]([NH:16][C@H:17]([C:22]([O:24][CH3:25])=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])=[O:15])[CH3:13])=O)C1C=CC=CC=1.[ClH:26].O>CO.[Pd]>[ClH:26].[NH2:11][C@@H:12]([C:14]([NH:16][C@H:17]([C:22]([O:24][CH3:25])=[O:23])[CH2:18][CH:19]([CH3:20])[CH3:21])=[O:15])[CH3:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 14278860Nalpha-Benzyloxycarbonyl-D-alanyl-L-leucine methyl ester

Product 1

HCID 88804173methyl (2S)-2-[(2R)-2-aminopropanamido]-4-methylpentanoate hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A solution of 7 g. of Nα -benzyloxycarbonyl-D-alanyl-L-leucine, methyl ester in 100 ml. of methanol and 22 ml. of 0.95 l N hydrogen chloride in methanol is stirred with 500 mg. of 20% palladium on carbon catalyst under hydrogen at one inch water pressure until thin layer chromatography of a sample shows complete conversion (three to six hours). The solution is filtered to remove the catalyst and is evaporated to a foam. Solution in chloroform, 50 ml., and precipitation by ethyl ether affords an oil which is collected and dried at 45° C. and 1 mm. pressure. The oil is used in the next step without further purification.

Workup

  1. customconversion (three to six hours)
  2. filtrationThe solution is filtered
  3. customto remove the catalyst
  4. customis evaporated to a foam
  5. custom, and precipitation by ethyl ether
  6. customaffords an oil which
  7. customis collected
  8. customdried at 45° C.
  9. customThe oil is used in the next step without further purification

Sources & evidence

ORD record
ord-6617b4a564cf457c91fad5dc9dad6782
Source dataset
uspto-grants-1978_09
Patent number
US04111923

Reaction notes

Loading…