Ethyl N-{[3-phenyl-5-(1H-pyrrol-1-yl)-1H-indol-2-yl]carbonyl}-L-phenylalaninate → n-{[3-Phenyl-5-(1h-pyrrol-1-yl)-1h-indol-2-yl]carbonyl}-l-phenylalanine

HRID 915353Notes

Reaction equation

HRID 915353 reaction equation
[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([N:16]4[CH:20]=[CH:19][CH:18]=[CH:17]4)[CH:14]=3)[NH:9][C:8]=2[C:21]([NH:23][C@H:24]([C:32]([O:34]CC)=[O:33])[CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>O>[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([N:16]4[CH:17]=[CH:18][CH:19]=[CH:20]4)[CH:14]=3)[NH:9][C:8]=2[C:21]([NH:23][C@H:24]([C:32]([OH:34])=[O:33])[CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[O:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 69340889Ethyl N-{[3-phenyl-5-(1H-pyrrol-1-yl)-1H-indol-2-yl]carbonyl}-L-phenylalaninate

Product 1

HCID 11339875n-{[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 ethyl N-{[3-phenyl-5-(1H-pyrrol-1-yl)-1H-indol-2-yl]carbonyl}-L-phenylalaninate followed the procedure of Example 1 Step 4 as an off-white solid: 1H NMR (DMSO-d6) δ 2.90 (dd, J=14.0, 6.1 Hz, 1 H), 3.09 (dd, J=14.0, 9.0 Hz, 1 H), 4.65 (dd, J=9.0, 6.1 Hz, 1 H), 6.20 (t, J=2.0 Hz, 1 H), 6.95-7.05 (m, 1 H), 7.15-7.60 (m, 16 H), 11.87 (s, 1 H), 12.91 (br s, 1 H); MS (ESI) m/z 450 (MH+); MS (ESI) m/z 448 ([M-H]−); HRMS calcd for C28H24N3O3: 450.1818; found (ESI+): 450.1809; Anal. calcd for C28H23N3O3.0.5 H2O: C, 73.35; H, 5.28; N, 9.16. Found: C, 73.27; H, 4.94; N, 9.37.

Sources & evidence

ORD record
ord-b3e6f141c09a4f71bf90ba30c81fd04e
Source dataset
uspto-grants-2007_09
Patent number
US07265148B2

Reaction notes

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