Trifluoroacetic acid → 2-amino-3-(1H-indol-3-yl)-N-(2-methoxybenzyl)propanamide

HRID 965176Notes

Reaction equation

C(OC([NH:8][CH:9]([CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)[C:10]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21])=[O:11])=O)(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>O>[NH2:8][CH:9]([CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)[C:10]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21])=[O:11]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of the 2-t-butoxycarbonylamino-3-(1H-indol-3-yl)-N-(2-methoxybenzyl)propanamide prepared supra (25.1 g, 59.2 mmol) and anisole (12 ml, 110.4 mmol) at 0° C. was added dropwise an aqueous solution of trifluoroacetic acid (118 ml, 1.53 mol) in 50 ml of water. This mixture was stirred for one hour at 0° C., followed by stirring for about 2.5 hours at ambient temperature, The mixture was then refrigerated for about 16 hours.

Workup

stirringby stirring for about 2.5 hours at ambient temperature
waitThe mixture was then refrigerated for about 16 hours

Sources & evidence

ORD record: ord-93b21aca79cf480590b86c8a5f5c3311
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05773441

Reaction notes

Loading…