benzyl N-[(2S)-1-amino-3-(1H-indol-3-yl)-1-oxopropan-2-yl]carbamate → L-Tryptophanamide

HRID 1746588Notes

Reaction equation

HRID 1746588 reaction equation
C(OC([NH:11][C@H:12]([C:23]([NH2:25])=[O:24])[CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)=O)C1C=CC=CC=1.[H][H]>[Pd].CO>[NH2:11][C@H:12]([C:23]([NH2:25])=[O:24])[CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1

Participants

5

Reactant 2

HCID 853880benzyl N-[(2S)-1-amino-3-(1H-indol-3-yl)-1-oxopropan-2-yl]carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 439356L-TryptophanamideYield 96.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To methanol (300 mL) solution of the compound obtained in Example 125 (3.6 g) was added 5% palladium/carbon (0.36 g) in an argon atmosphere, and the mixture was stirred for 16 hours at room temperature in a hydrogen atmosphere. The catalyst was filtered off, and the solvent was distilled off under a reduced pressure, to give the captioned compound (2.1 g, 95%) as an oily product.

Workup

  1. filtrationThe catalyst was filtered off
  2. distillationthe solvent was distilled off under a reduced pressure

Sources & evidence

ORD record
ord-21aa14b37a5e46d8b9bb1e0555ac93a1
Source dataset
uspto-grants-2015_10
Patent number
US09150510B2

Reaction notes

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