Ethyl L-phenylalaninate hydrochloride → N-{[1-benzyl-3-phenyl-5-(1H-pyrrol-1-yl)-1H-indol-2-yl]carbonyl}-L-phenylalanine

HRID 915343Notes

Reaction equation

HRID 915343 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N:17]3[CH:21]=[CH:20][CH:19]=[CH:18]3)=[CH:14][CH:15]=2)[C:10]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:9]1[C:28](O)=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C([O:34][C:35](=[O:45])[C@H:36]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[NH2:37])C>O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N:17]3[CH:18]=[CH:19][CH:20]=[CH:21]3)=[CH:14][CH:15]=2)[C:10]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[C:9]1[C:28]([NH:37][C@H:36]([C:35]([OH:34])=[O:45])[CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)=[O:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 165085Ethyl L-phenylalaninate hydrochlorideHCID 114861671-benzyl-3-phenyl-5-(1H-pyrrol-1-yl)-1H-indole-2-carboxylic acid

Product 1

HCID 11786025N-{[1-benzyl-3-phenyl-5-(1H-pyrrol-1-yl)-1H-indol-2-yl]carbonyl}-L-phenylalanine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared from 1-benzyl-3-phenyl-5-(1H-pyrrol-1-yl)-1H-indole-2-carboxylic acid and L-phenylalanine ethyl ester hydrochloride followed the procedure of Example 2 Step 4 as an off-white solid: 1H NMR (DMSO-d6) δ 2.90 (dd, J=13.8, 10.7 Hz, 1 H), 3.17 (dd, J=13.8, 4.3 Hz, 1H), 4.65-4.75 (m, 1 H), 5.23 (d, J=16.2 Hz, 1 H), 5.53 (d, J=16.2 Hz, 1 H), 6.21 (t, J=3.9 Hz, 2 H), 7.10-7.50 (m, 18 H), 7.57 (d, J=9.8 Hz, 1 H), 7.64 (d, J=1.9 Hz, 1 H), 9.09 (d, J=8.0 Hz, 1 H), 12.93 (br s, 1 H); MS (ESI) m/z 540 (MH+); MS (ESI) m/z 538 ([M-H]−); HRMS calcd for C35H30N3O3: 540.2288; found (ESI+): 540.2277; Anal. calcd for C35H29N3O3.0.4 H2O: C, 76.88; H, 5.49; N, 7.68. Found: C, 76.68; H, 5.24; N, 7.87.

Sources & evidence

ORD record
ord-43865b5dfeea40de86c98f55fc124bab
Source dataset
uspto-grants-2007_09
Patent number
US07265148B2

Reaction notes

Loading…