Water → Ethyl 3-(3-aminoazetidin-1-yl)benzoate

HRID 1425359Notes

Reaction equation

HRID 1425359 reaction equation
P(=O)(O)(O)O.C(OC([NH:13][CH:14]1[CH2:17][N:16]([C:18]2[CH:19]=[C:20]([CH:26]=[CH:27][CH:28]=2)[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:15]1)=O)(C)(C)C.O.[OH-].[Na+]>ClCCl>[NH2:13][CH:14]1[CH2:15][N:16]([C:18]2[CH:19]=[C:20]([CH:26]=[CH:27][CH:28]=2)[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 1004Phosphoric AcidHCID 14798Sodium HydroxideHCID 68405850Ethyl 3-{3-[(tert-butoxycarbonyl)amino]azetidin-1-yl}benzoate

Product 1

HCID 67549209Ethyl 3-(3-aminoazetidin-1-yl)benzoateYield 83.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

85% phosphoric acid (0.18 mL, 1.57 mmol) was added to a solution of ethyl 3-{3-[(tert-butoxycarbonyl)amino]azetidin-1-yl}benzoate obtained in Example (223a) (200 mg, 0.62 mmol) in dichloromethane (0.8 mL) at room temperature, followed by stirring for 27 hours. Water and a 50% aqueous sodium hydroxide solution were added to the reaction solution, and then the mixture was extracted with chloroform. The combined organic layers were dried over anhydrous magnesium sulfate and filtered. Thereafter, the solvent was evaporated under reduced pressure to obtain 114 mg of the title compound as a colorless oily substance (83%).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customThereafter, the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1914fd308f5d4ec9ab2362a96ae9d4cd
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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