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

HRID 2074347Notes

Reaction equation

HRID 2074347 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.CN(C=O)C.[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)propanamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21901440N,N-dimethylformamide methanolSolvent

Procedure

Same procedure as above with Z-Trp-NHCH2Ph (616 mg, 1.44 mmol), 10% Pd/C (153 mg) in MeOH/DMF (14.5 mL, 1/1). After purification by flash chromatography on silica gel (3-12% MeOH/CH2Cl2), Trp-NHCH2Ph was isolated as a pale yellow oil (351 mg, 83%). 1H NMR (300 MHz, CDCl3) δ 2.98 (dd, J=14.4 Hz, J=8.7 Hz, 1H, CH2), 3.44 (dd, J=14.4 Hz, J=4.1 Hz, 1H, CH2), 3.80 (dd, J=8.7 Hz, J=4.2 Hz, 1H, CHα), 4.46 (m, 2H, CH2 (Bn)), 7.06 (d, J=2.1 Hz, 1 aromatic H), 7.13-7.36 (m, 7 aromatic H), 7.41 (d, J=8 Hz, 1 aromatic H), 7.61 (m, 1H, NH amide), 7.72 (d, J=7.8 Hz, 1 aromatic H), 8.3 (broad s, 1H, NH indole). 13C NMR (75 MHz, MeOD) δ 30.5 (CH2 Trp), 42.7 (CH2 Ph), 55.4 (CHα), 109.3, 111, 118.1, 118.5, 121.2, 123.5, 126.8, 127, 127.1, 127.4, 128, 128.1, 136.8, 138 (14 aromatic C), 174.6 (CO amide).

Workup

  1. customAfter purification by flash chromatography on silica gel (3-12% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-2ca73fc4bfab4efa81de5199dec6bde3
Source dataset
uspto-grants-2011_04
Patent number
US07919468B2

Reaction notes

Loading…