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

HRID 1379045Notes

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 mmoles) and anisole (12 ml, 110.4 mmoles) at 0° C. was added dropwise an aqueous solution of trifluoroacetic acid (118 ml, 1.53 moles) 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-95faced240864ae4be1829491502df0f
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05670499

Reaction notes

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