Hydrochloric Acid → isopropyl (2RS, 3S)-3-(L-alanyl)amino-2-hydroxy-5-methylhexanoate hydrochloride

HRID 1722184Notes

Reaction equation

HRID 1722184 reaction equation
C(OC([NH:11][C@H:12]([C:14]([NH:16][C@@H:17]([CH2:26][CH:27]([CH3:29])[CH3:28])[CH:18]([OH:25])[C:19]([O:21][CH:22]([CH3:24])[CH3:23])=[O:20])=[O:15])[CH3:13])=O)C1C=CC=CC=1.[ClH:30]>CO.[Pd]>[ClH:30].[NH2:11][C@H:12]([C:14]([NH:16][C@@H:17]([CH2:26][CH:27]([CH3:29])[CH3:28])[CH:18]([OH:25])[C:19]([O:21][CH:22]([CH3:23])[CH3:24])=[O:20])=[O:15])[CH3:13]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86743281isopropyl (2RS, 3S)-3-(N-benzyloxycarbonyl-L-alanyl)amino-2-hydroxy-5-methylhexanoate

Product 1

HCID 14070611isopropyl (2RS, 3S)-3-(L-alanyl)amino-2-hydroxy-5-methylhexanoate hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 56 mg of the isopropyl hexanoate compound in 3ml of methanol were added 0.2 ml of a 2N-hydrochloric acid and 20 mg of a 10% of palladium charcoal, and the mixture was hydrogenated under a hydrogen atmosphere. After filtration of the catalyst, the filtrate was evaporated under reduced pressure to obtain 42 mg of isopropyl (2RS, 3S)-3-(L-alanyl)amino-2-hydroxy-5-methylhexanoate hydrochloride as a colorless viscous oil.

Workup

  1. filtrationAfter filtration of the catalyst
  2. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1352e4ea3dde4158b0a8682d7b07eabc
Source dataset
uspto-grants-1989_08
Patent number
US04853463

Reaction notes

Loading…