Z-Trp-NHPh → (S)-2-Amino-3-(1H-indol-3-yl)-N-phenylpropanamide

HRID 2074346Notes

Reaction equation

HRID 2074346 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:13]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=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>[Pd]>[NH2:1][C@H:2]([C:13]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=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

3

Reactant 1

HCID 1131238Z-Trp-NHPh

Product 1

HCID 16735217(S)-2-Amino-3-(1H-indol-3-yl)-N-phenylpropanamide

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A Schlenk flask charged with Z-Trp-NHPh (1.7 g, 4.11 mmol) and 10% Pd/C (437.4 mg) was flushed under H2 before adding MeOH/DMF (41 mL, 1/1). The reaction mixture was stirred under atmosphere of H2 overnight followed by filtration through a pad of celite. The solvent was removed in vacuo and the crude was purified by flash column chromatography on silica gel (2-8% MeOH/CH2Cl2). The amine was isolated as a yellow solid (841 mg, 73%). mp 114-116° C. 1H NMR (300 MHz, CDCl3) δ 1.89 (broad s, 2H, NH2), 3.06 (dd, J=14.5 Hz, J=8.8 Hz, 1H, CH2), 3.55 (dd, J=14.5 Hz, J=3.9 Hz, 1H, CH2), 3.89 (dd, J=8.8 Hz, J=3.8 Hz, 1H, CHα), 7.06-7.41 (m, 7 aromatic H), 7.61 (d, J=7.9 Hz, 2 aromatic H), 7.72 (d, J=7.8 Hz, 1 aromatic H), 8.24 (broad s, 1H, NH amide), 9.48 (s, 1H, NH indole). 13C NMR (75 MHz, CDCl3) δ 30.5 (CH2 Trp), 56 (CHα), 111.4, 118.8, 119.5, 119.7, 122.3, 123.2, 124.1, 127.5, 129, 129.1, 136.5, 137.8 (14 aromatic C), 173.2 (CO amide).

Workup

  1. customwas flushed under H2
  2. additionbefore adding MeOH/DMF (41 mL, 1/1)
  3. filtrationfollowed by filtration through a pad of celite
  4. customThe solvent was removed in vacuo
  5. customthe crude was purified by flash column chromatography on silica gel (2-8% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-7d07e04c16564befaf94ae8c1742b905
Source dataset
uspto-grants-2011_04
Patent number
US07919468B2

Reaction notes

Loading…