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

HRID 2086751Notes

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-6bc8e69f0104435fa5395d7e0336f585
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06727255B1

Reaction notes

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