Hydrochloric Acid → D-Tryptophyl-L-leucine methyl ester hydrochloride

HRID 2083840Notes

Reaction equation

HRID 2083840 reaction equation
[CH3:1][O:2][C:3](=[O:34])[C@H:4]([CH2:30][CH:31]([CH3:33])[CH3:32])[NH:5][C:6](=[O:29])[C@@H:7]([CH2:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22][CH:21]=1)[NH:8]C(OCC1C=CC=CC=1)=O.[ClH:35].[H][H]>[Pd].CO>[ClH:35].[CH3:1][O:2][C:3](=[O:34])[C@H:4]([CH2:30][CH:31]([CH3:32])[CH3:33])[NH:5][C:6](=[O:29])[C@@H:7]([CH2:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22][CH:21]=1)[NH2:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 54062429Nalpha-benzyloxycarbonyl-D-tryptophyl-L-leucine methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 70625668D-Tryptophyl-L-leucine methyl ester hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Nα -Benzyloxycarbonyl-D-tryptophyl-L-leucine methyl ester, 2.75 g., and 2.65 ml. of 2.23 N hydrogen chloride are dissolved in 100 ml. of methanol followed by the addition of 300 mg. of 10% palladium-on-carbon. The reaction is stirred under a hydrogen atmosphere with hydrogen bubbling through the mixture for seventy minutes. Thin layer chromatography indicates the reaction to be complete in about 20 minutes. The mixture is filtered and the solvent evaporated. The residue is dried under reduced pressure, 2.21 g. of D-tryptophyl-L-leucine methyl ester hydrochloride, [α]D23 -73° (c 1.02, methanol).

Workup

  1. customthe reaction
  2. filtrationThe mixture is filtered
  3. customthe solvent evaporated
  4. customThe residue is dried under reduced pressure, 2.21 g

Sources & evidence

ORD record
ord-8c2c3510ed214cce9a942f746b1baed1
Source dataset
uspto-grants-1978_04
Patent number
US04086219

Reaction notes

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