Hydrochloric Acid → Hydrochloric Acid

HRID 982606

Reaction equation

HRID 982606 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@@H:2]([C:13]([NH2:15])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[ClH:26].O>CN(C=O)C.[Pd]>[ClH:26].[NH2:1][C@@H:2]([C:13]([NH2:15])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 853881Z-D-Trp-NH2

Product 2

HCID 313Hydrochloric AcidHCID 688582D-tryptophanamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

Z-D-Trp-NH2 (3 g; 8.9 mmol; 1 eq.) was dissolved in DMF (100 ml). HCl 36% (845 μl; 1.1 eq.), water (2 ml) and palladium on activated charcoal (95 mg, 0.1 eq.) were added to the stirred mixture. The solution was bubbled under hydrogen for 24 hr. When the reaction went to completion, the palladium was filtered on celite. The solvent was removed in vacuo to afford HCl, H-D-Trp-NH2 as a colorless oil.

Workup

  1. customThe solution was bubbled under hydrogen for 24 hr
  2. filtrationthe palladium was filtered on celite
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-737ff3e68d314d74b8635aaef02a34a8
Source dataset
uspto-grants-2005_03
Patent number
US06861409B2

Linked notes

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