Hydrochloric Acid → Hydrochloric Acid

HRID 1593367

Reaction equation

HRID 1593367 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-0c7c0ca825d1497d922649204cb53b3a
Source dataset
uspto-grants-2007_11
Patent number
US07297681B2

Linked notes

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