Hydrochloric Acid → H-Tyr(But)-Gly-OEt.HCl

HRID 1154151Notes

Reaction equation

HRID 1154151 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:15]([NH:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:16])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][CH:5]=1.[H][H].[ClH:36]>CO>[NH2:1][C@H:2]([C:15]([NH:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:16])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][CH:5]=1.[ClH:36]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 13178769Z-Tyr(But)-Gly-OEtHCID 178418361HCID 178418361, compound

Product 1

HCID 131714055H-Tyr(But)-Gly-OEt.HCl

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

19.78 g (43 mmoles) of Z-Tyr(But)-Gly-OEt are dissolved in 200 ml of methanol. A Pd-on-charcoal catalyst is added to this solution and hydrogen is passed through the solution while stirring and adding approx. 2N methanolic HCL at pH 4.5 (autotitrator), until no further methanolic HCl is taken up. The catalyst is then filtered off and the filtrate is concentrated. The residue is stirred with ether and suction-drained. Yield 14.87 g (93.7%), melting point 140°-142°, [α]D22 =+30.9° (c=1, methanol).

Workup

  1. additionadding approx. 2N methanolic HCL at pH 4.5 (autotitrator)
  2. filtrationThe catalyst is then filtered off
  3. concentrationthe filtrate is concentrated
  4. stirringThe residue is stirred with ether
  5. customYield 14.87 g (93.7%), melting point 140°-142°, [α]D22 =+30.9° (c=1, methanol)

Sources & evidence

ORD record
ord-8afd7905893541adbb8253e9c1edf835
Source dataset
uspto-grants-1984_12
Patent number
US04487764

Reaction notes

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