2-Methoxybenzylamine → 2-t-butoxycarbonylamino-3-(1H-indol-3-yl)-N-(2-methoxybenzyl)propanamide

HRID 965175Notes

Reaction equation

HRID 965175 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:20]([OH:22])=O)[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(C1NC=CN=1)(C1NC=CN=1)=O.[CH3:35][O:36][C:37]1[CH:44]=[CH:43][CH:42]=[CH:41][C:38]=1[CH2:39][NH2:40]>O1CCOCC1>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)[C:20]([NH:40][CH2:39][C:38]1[CH:41]=[CH:42][CH:43]=[CH:44][C:37]=1[O:36][CH3:35])=[O:22])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 812922-MethoxybenzylamineHCID 83169N-tert-Butoxycarbonyl-L-tryptophanHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 107884072-t-butoxycarbonylamino-3-(1H-indol-3-yl)-N-(2-methoxybenzyl)propanamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-(t-butoxycarbonyl)tryptophan (46.4 g, 152.6 mmol) in 500 ml of dioxane was added carbonyl diimidazole (25.4 g, 156 mmol) in a portionwise manner. The resulting mixture was stirred for about 2.5 hours at room temperature and then stirred at 45° C for 30 minutes. Next, 2-methoxybenzylamine (20.7 ml, 158.7 mmol) was added and the reaction mixture was then stirred for 16 hours at room temperature.

Workup

  1. stirringstirred at 45° C for 30 minutes
  2. stirringthe reaction mixture was then stirred for 16 hours at room temperature

Sources & evidence

ORD record
ord-77f9dbc981ae4cbb877ed08bfbba906a
Source dataset
uspto-grants-1998_06
Patent number
US05773441

Reaction notes

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