Water → Ethyl 2-(3-aminoazetidin-1-yl)-4-isopropyl-1,3-thiazole-5-carboxylate

HRID 1425351Notes

Reaction equation

HRID 1425351 reaction equation
P(=O)(O)(O)O.C(OC([NH:13][CH:14]1[CH2:17][N:16]([C:18]2[S:19][C:20]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:21]([CH:23]([CH3:25])[CH3:24])[N:22]=2)[CH2:15]1)=O)(C)(C)C.O.[OH-].[Na+]>ClCCl>[NH2:13][CH:14]1[CH2:17][N:16]([C:18]2[S:19][C:20]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:21]([CH:23]([CH3:25])[CH3:24])[N:22]=2)[CH2:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 1004Phosphoric AcidHCID 14798Sodium HydroxideHCID 67548483Ethyl 2-{3-[(tert-butoxycarbonyl)amino]azetidin-1-yl}-4-isopropyl-1,3-thiazole-5-carboxylate

Product 1

HCID 67548973Ethyl 2-(3-aminoazetidin-1-yl)-4-isopropyl-1,3-thiazole-5-carboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

85% phosphoric acid (0.14 mL, 1.18 mmol) was added to a solution of ethyl 2-{3-[(tert-butoxycarbonyl)amino]azetidin-1-yl}-4-isopropyl-1,3-thiazole-5-carboxylate obtained in Example (221a) (175 mg, 0.47 mmol) in dichloromethane (1 mL) at room temperature, followed by stirring for 15.5 hours. Water and a 50% aqueous sodium hydroxide solution were added to the reaction solution, and then the mixture was extracted with a chloroform/methanol mixed solvent. The combined organic layers were dried over anhydrous magnesium sulfate and filtered. Thereafter, the solvent was evaporated under reduced pressure to obtain 95 mg of the title compound as a colorless oily substance (74%).

Workup

  1. extractionthe mixture was extracted with a chloroform/methanol mixed solvent
  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-a21c3e38dd1747d28d4138d502af9771
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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