1,4-Dioxane hydrochloride → (2S,2'S)-N,N'-(biphenyl-2,2'-diyl)dipyrrolidine-2-carboxamide

HRID 75089Notes

Reaction equation

HRID 75089 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13](=[O:38])[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[NH:27][C:28]([C@@H:30]1[CH2:34][CH2:33][CH2:32][N:31]1C([O-])=O)=[O:29])=O)(C)(C)C.Cl.O1CCOCC1>>[C:16]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[NH:27][C:28]([C@@H:30]2[CH2:34][CH2:33][CH2:32][NH:31]2)=[O:29])[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[NH:14][C:13]([C@@H:9]1[CH2:10][CH2:11][CH2:12][NH:8]1)=[O:38]

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 131731868(2S,2'S)-tert-butyl-2,2'-(biphenyl-2,2'-diylbis(azanediyl))bis(oxomethylene)dipyrrolidine-1-carboxylate

Product 1

HCID 66982727(2S,2'S)-N,N'-(biphenyl-2,2'-diyl)dipyrrolidine-2-carboxamide

Procedure

(2S,2′S)-tert-butyl-2,2′-(biphenyl-2,2′-diylbis(azanediyl))bis(oxomethylene)dipyrrolidine-1-carboxylate d (0.140 g, 0.24 mmol) was suspended in a solution of 4M HCl/dioxane and stirred at room temperature for 4 h until LCMS indicated complete deprotection. The reaction mixture was concentrated to give (2S,2′S)—N,N′-(biphenyl-2,2′-diyl)dipyrrolidine-2-carboxamide e (0.09 g, 100%). LC/MS: mw 378.47; M+H+=379.2.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-a935ee1279424320922e8dac932e6913
Source dataset
uspto-grants-2014_09
Patent number
US08835393B2

Reaction notes

Loading…