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

HRID 865499Notes

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-d8d869ce919540dbb1a6266d3462611f
Source dataset: uspto-grants-1996_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05565568

Reaction notes

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