Hydrochloric Acid → H-Val-Val-OMe.HCl

HRID 904947

Reaction equation

HRID 904947 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:6]([NH:8][C@H:9]([C:13]([O:15][CH3:16])=[O:14])[CH:10]([CH3:12])[CH3:11])=[O:7])[CH:3]([CH3:5])[CH3:4].[ClH:27]>CO>[NH2:1][C@H:2]([C:6]([NH:8][C@H:9]([C:13]([O:15][CH3:16])=[O:14])[CH:10]([CH3:11])[CH3:12])=[O:7])[CH:3]([CH3:5])[CH3:4].[ClH:27]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 12286262Z-Val-Val-OMe

Product 1

HCID 12944633H-Val-Val-OMe.HCl

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

30 g of Z-Val-Val-OMe (prepared as in Chem. Ber. 103, 788-798 (1970)) are dissolved in 250 ml of methanol and subjected to catalytic hydrogenation at pH 4 after adding methanolic hydrochloric acid and Pd-on-BaSO4. When the reaction is complete, the catalyst is filtered off and the filtrate is concentrated. The resulting oil is triturated with ether. The substance crystallizes after a little time. It is filtered off and rinsed with ether. The substance is hygroscopic and is dried over P2O5 in vacuo. Yield 18.8 g, melting point 153°. [α]D23 =+2.5° (c=1, in methanol).

Workup

  1. filtrationthe catalyst is filtered off
  2. concentrationthe filtrate is concentrated
  3. customThe resulting oil is triturated with ether
  4. customThe substance crystallizes after a little time
  5. filtrationIt is filtered off
  6. washrinsed with ether
  7. dry with materialis dried over P2O5 in vacuo
  8. custom[α]D23 =+2.5° (c=1, in methanol)

Sources & evidence

ORD record
ord-0afbe2531c7e4503896d1af487b74ed8
Source dataset
uspto-grants-1983_12
Patent number
US04420424

Linked notes

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