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

HRID 915352Notes

Reaction equation

HRID 915352 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](O)=[O:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH2:25]([O:27][C:28](=[O:38])[C@H:29]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[NH2:30])[CH3:26]>>[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:30][C@H:29]([C:28]([O:27][CH2:25][CH3:26])=[O:38])[CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:22])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 165085Ethyl L-phenylalaninate hydrochlorideHCID 113924663-phenyl-5-(1H-pyrrol-1-yl)-1H-indole-2-carboxylic acid

Product 1

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

Procedure

Ethyl N-{[3-phenyl-5-(1H-pyrrol-1-yl)-1H-indol-2-yl]carbonyl}-L-phenylalaninate was prepared from 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 a pale yellowish solid: 1H NMR (DMSO-d6) δ 1.12 (t, J=7.0 Hz, 3 H), 2.93 (dd, J=13.5, 6.2 Hz, 1 H), 3.05 (dd, J=13.5, 8.0 Hz, 1H), 4.08 (q, J=7.0 Hz, 2 H), 4.70 (dd, J=8.0, 6.2 Hz, 1 H 6.21 (t, J=2.0 Hz, 1 H), 6.95-7.05 (m, 1 H), 7.20-7.60 (m, 16 H), 11.89 (s, 1 H); MS (ESI) m/z 478 (MH+); MS (ESI) m/z 476 ([M-H]−); HRMS calcd for C30H28N3O3: 478.2131; found (ESI+): 478.2113; Anal. calcd for C30H27N3O3: C, 75.45; H, 5.70; N, 8.80. Found: C, 75.30; H, 5,79; N, 8.72.

Sources & evidence

ORD record
ord-bcd07982e99848c8b1f7b2966b32c849
Source dataset
uspto-grants-2007_09
Patent number
US07265148B2

Reaction notes

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