Cbz-Trp-NHBn → (S)-2-Amino-N-benzyl-3-(1H-indol-3-yl)propanamide

HRID 129717Notes

Reaction equation

HRID 129717 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:13]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[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>CO.[Pd]>[NH2:1][C@H:2]([C:13]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[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

4

Reactant 1

HCID 16735215Cbz-Trp-NHBn

Product 1

HCID 775625(S)-2-Amino-N-benzyl-3-(1H-indol-3-yl)propanamideYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2.20 g (5.15 mmol) Cbz-Trp-NHBn in 60 mL of MeOH was subjected to hydrogenolysis over Pd/C to give 1.43 g (4.88 mmol, 95%) of Trp-NHBn. Characteristic analytical data are as follows: mp 112°-114° C.; 1H NMR (300 MHz, CDCl3) δ8.40-7.00 (m, 11H, Ar), 4.44 (d, J=6 Hz, 2H, CH2 --N), 3.77 (dd, J=4 Hz, 9H, H-α), 3.42 (dd, J=4, 14 Hz, 1H, H-β), 2.98 (dd, J=9, 14 Hz, 1H, H-β); mass spectrum (EI), m/e 293 (M+), 277 (M+ -NH2), 130 (M+ --H2N--CH--CONH--Bn); [α]25D +42.1° (c=1.02, MeOH).

Sources & evidence

ORD record
ord-ee18ca73585f48cb9a2bccd79eabd18f
Source dataset
uspto-grants-1995_11
Patent number
US05470834

Reaction notes

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