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

HRID 2118124Notes

Reaction equation

HRID 2118124 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-])=O)=[CH:8][CH:9]=2)[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:3]1[C:20](O)=[O:21].Cl.[CH2:24]([O:26][C:27](=[O:37])[C@H:28]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[NH2:29])[CH3:25]>>[NH2:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:2]([CH3:1])[C:3]([C:20]([NH:29][C@H:28]([C:27]([O:26][CH2:24][CH3:25])=[O:37])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:21])=[C:4]2[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 165085Ethyl L-phenylalaninate hydrochlorideHCID 215435181-Methyl-5-nitro-3-phenyl-1H-indole-2-carboxylic acid

Product 1

HCID 69228463Ethyl N-[(5-amino-1-methyl-3-phenyl-1H-indol-2-yl)carbonyl]-L-phenylalaninate

Procedure

Ethyl N-[(5-amino-1-methyl-3-phenyl-1H-indol-2-yl)carbonyl]-L-phenylalaninate was prepared from 1-methyl-5-nitro-3-phenyl-1H-indole-2-carboxylic acid and L-phenylalanine ethyl ester hydrochloride followed the procedure of Example 8 Step 2 as a pale yellow solid: MS (ESI) m/z 442 (MH+); HRMS calcd for C27H28N3O3: 442.2128; found (ESI+): 442.2122.

Sources & evidence

ORD record
ord-1f85226ef43d4425b37c021a8483c6e5
Source dataset
uspto-grants-2008_10
Patent number
US07442805B2

Reaction notes

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