Hydrochloric Acid → (2S)-2-amino-N-[(2S)-1-amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]-3-phenylpropanamide

HRID 1904037Notes

Reaction equation

HRID 1904037 reaction equation
Cl.[NH:2](C(OCC1C=CC=CC=1)=O)[C@H:3]([C:11]([NH:13][C@H:14]([C:23]([NH2:25])=[O:24])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CO.[C].[Pd]>[NH2:2][C@H:3]([C:11]([NH:13][C@H:14]([C:23]([NH2:25])=[O:24])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)=[O:12])[CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 7073086HCID 7073086, compound

Product 1

HCID 7020145(2S)-2-amino-N-[(2S)-1-amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]-3-phenylpropanamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 178418390HCID 178418390, compoundSolvent

Procedure

The hydrochloride named above can be prepared in the following manner: 4.62 g of Z-Phe-Tyr-NH2 are hydrogenated in 50 ml of methanol in the presence of 4 ml of hydrochloric acid in methanol (2.53 N) and 0.5 g of palladium-carbon (10%). After filtering the catalyst and evaporating the filtrate the HCl.H-Phe-Tyr-NH2 is obtained as a white foam. Rf-value on silicagel (with chloroform-methanol) is 0.42.

Workup

  1. customabove can be prepared in the following manner
  2. filtrationAfter filtering the catalyst
  3. customevaporating the filtrate the HCl

Sources & evidence

ORD record
ord-ec37db0baa4941d28f97cc01bf81d762
Source dataset
uspto-grants-1984_03
Patent number
US04439425

Reaction notes

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