Sodium Hydroxide → Ethyl 2-[3-(aminomethyl)-1-azetidinyl]-4-methyl-5-thiazolecarboxylate

HRID 43912Notes

Reaction equation

HRID 43912 reaction equation
Br.C(O)(=O)C.C(OC([NH:16][CH2:17][CH:18]1[CH2:21][N:20]([C:22]2[S:23][C:24]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:25]([CH3:27])[N:26]=2)[CH2:19]1)=O)C1C=CC=CC=1.[OH-].[Na+]>C(O)(=O)C>[NH2:16][CH2:17][CH:18]1[CH2:21][N:20]([C:22]2[S:23][C:24]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:25]([CH3:27])[N:26]=2)[CH2:19]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 67549285HCID 67549285, compound

Product 1

HCID 67549202Ethyl 2-[3-(aminomethyl)-1-azetidinyl]-4-methyl-5-thiazolecarboxylateYield 60.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 30% hydrogen bromide/acetic acid solution (0.64 mL, 3.29 mmol) was added to a solution of ethyl 2-[3-({[(benzyloxy)carbonyl]amino}methyl)azetidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate obtained in Example (233b) (128 mg, 0.33 mmol) in acetic acid (1 mL), and the mixture was stirred at room temperature for 100 minutes. A 1 N aqueous sodium hydroxide solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate and filtered. Thereafter, the filtrate was concentrated under reduced pressure to obtain 51 mg of the title compound as a colorless oily substance (61%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationThereafter, the filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1cdfad84d9434ffdb649ae79574d1476
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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