Hydrochloric Acid → HCID 13772581, compound

HRID 235727Notes

Reaction equation

HRID 235727 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:35])[C:12]([NH:14][CH2:15][CH:16]([OH:34])[CH2:17][NH:18][C:19](=[O:33])[C@H:20]([CH3:32])[NH:21]C(OCC2C=CC=CC=2)=O)=[O:13])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[ClH:36]>CO.[Pd]>[ClH:36].[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([CH3:35])[C:12]([NH:14][CH2:15][CH:16]([OH:34])[CH2:17][NH:18][C:19](=[O:33])[C@H:20]([CH3:32])[NH2:21])=[O:13])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 13772579HCID 13772579, compound

Product 1

HCID 13772581HCID 13772581, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a manner analogous to that described in Stage 15.4, from 3.24 g (6.7 mmol) of N-benzyloxycarbonyl-L-alanine-3-[2-(4-isobutylphenyl)-propionylamino]-2-hydroxypropylamide by means of catalytic hydrogenation [1 g of palladium-on-carbon (10% palladium), 15 minutes, room temperature, normal pressure] in methanol at pH 7 (titration with 1N hydrochloric acid), there is obtained L-alanine-3-[2-(4-isobutylphenyl)-propionylamino]-2-hydroxypropylamide hydrochloride in the form of colourless crystals which decompose at 88° and above (triturated with diethyl ether) and contain 0.43 mol of water; [α]D20 =+8.3± 0.9° (c=1.065; methanol), Rf =0.30 (chloroform:methanol=4:1), Rf =0.58 (chloroform:methanol:water=70:30:5).

Sources & evidence

ORD record
ord-b12cbdd447d949b1a890d13540e88138
Source dataset
uspto-grants-1987_02
Patent number
US04640911

Reaction notes

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