1,4-Dioxane hydrochloride → (S)-benzyl 2-(4-aminophenylcarbamoyl)pyrrolidine-1-carboxylate

HRID 1752538

Reaction equation

HRID 1752538 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C@@H:18]2[CH2:22][CH2:21][CH2:20][N:19]2[C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])=[O:17])=[CH:11][CH:10]=1)=O)(C)(C)C.O1CCOCC1.Cl>O1CCOCC1>[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C@@H:18]2[CH2:22][CH2:21][CH2:20][N:19]2[C:23]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[O:24])=[O:17])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 59396122(S)-benzyl 2-(4-(tert-butoxycarbonylamino)phenylcarbamoyl)pyrrolidine-1-carboxylate

Product 1

HCID 59396116(S)-benzyl 2-(4-aminophenylcarbamoyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of the Product from Example 3A (0.245 g, 0.56 mmol) in dioxane (5 mL) was added 4M HCl dioxane (2.8 mL, 11.2 mol) and the mixture was stirred at ambient temperature for 17 hours. The mixture was concentrated and azeotroped with toluene to five a tan solid (0.18 g, 86%).

Workup

  1. concentrationThe mixture was concentrated
  2. customazeotroped with toluene to five a tan solid (0.18 g, 86%)

Sources & evidence

ORD record
ord-36f016a6f41b4814a42681bcb9c1d8d5
Source dataset
uspto-grants-2015_10
Patent number
US09163017B2

Linked notes

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