1H-Indole-2-carboxylic acid, 1-methyl- → HCID 70144516, compound

HRID 2268807Notes

Reaction equation

HRID 2268807 reaction equation
Cl.C[O:3][C:4](=[O:24])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:23])=[CH:10][CH:9]=1)[NH2:6].[CH3:25][N:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[C:27]1C(O)=O>>[Cl:23][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([Cl:22])[C:16]=1[CH2:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][C@@H:5]([C:4]([OH:3])=[O:24])[NH:6][C:27]2[N:26]([CH3:25])[C:34]3[C:29]([CH:28]=2)=[CH:30][CH:31]=[CH:32][CH:33]=3)=[CH:9][CH:10]=1

Participants

3

Reactant 2

HCID 276951H-Indole-2-carboxylic acid, 1-methyl-HCID 69806827HCID 69806827, compound

Product 1

HCID 70144516HCID 70144516, compound

Procedure

from O-(2,6-dichlorobenzyl)-L-tyrosine methyl ester hydrochloride and 1-methylindole-2-carboxylic acid. Freeze drying afforded the title compound as a white amorphous solid (220 mg). δH (DMSO-d6) 11.7 (1H, br s), 8.66 (1H, d, J 8.3 Hz), 7.65 (1H, d, J 7.9 Hz), 7.53 (2H, app.d, J 8/1 Hz), 7.26 (1H, obscured m), 7.09 (2H, app.t, J 7.5 Hz), 6.96 (2H, d, J 8.5 Hz), 5.16 (2H, s), 4.64-4.54 (1H, m), 3.89 (3H, s), 3.16 (1H, dd, J 13.8, 4.3 Hz) and 3.00 (1H, dd, J 13.8, 10.4 Hz); m/z (ESI, 60V) 497 and 499 (MH+).

Workup

  1. customFreeze drying

Sources & evidence

ORD record
ord-5a872967b8894d868d85942fe3f099b3
Source dataset
uspto-grants-2001_12
Patent number
US06329372B1

Reaction notes

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