Nitrogen → 2-[5-(2-Methyl-[1,3]dioxolan-2-yl)-thiophen-2-ylmethyl]-oxazole-4-carboxylic acid

HRID 1189402Notes

Reaction equation

HRID 1189402 reaction equation
N#N.C[O:4][C:5]([C:7]1[N:8]=[C:9]([CH2:12][C:13]2[S:14][C:15]([C:18]3([CH3:23])[O:22][CH2:21][CH2:20][O:19]3)=[CH:16][CH:17]=2)[O:10][CH:11]=1)=[O:6].[OH-].[Na+]>C1COCC1.Cl>[C:18]([C:15]1[S:14][C:13]([CH2:12][C:9]2[O:10][CH:11]=[C:7]([C:5]([OH:6])=[O:4])[N:8]=2)=[CH:17][CH:16]=1)(=[O:19])[CH3:23].[CH3:23][C:18]1([C:15]2[S:14][C:13]([CH2:12][C:9]3[O:10][CH:11]=[C:7]([C:5]([OH:6])=[O:4])[N:8]=3)=[CH:17][CH:16]=2)[O:22][CH2:21][CH2:20][O:19]1

Participants

7

Reactant 3

HCID 947NitrogenHCID 14798Sodium HydroxideHCID 671285542-[5-(2-Methyl-[1,3]dioxolan-2-yl)-thiophen-2-ylmethyl]-oxazole-4-carboxylic acid methyl ester

Product 2

HCID 671284342-[5-(2-Methyl-[1,3]dioxolan-2-yl)-thiophen-2-ylmethyl]-oxazole-4-carboxylic acidHCID 671286602-(5-Acetyl-thiophen-2-ylmethyl)-oxazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-[5-(2-methyl-[1,3]dioxolan-2-yl)-thiophen-2-ylmethyl]-oxazole-4-carboxylic acid methyl ester (570 mg, 1.84 mmol) in THF (20 mL) was treated at rt with 1N NaOH (10 mL, 10.00 mmol) and the reaction mixture was stirred for 1 h at rt. The reaction mixture was poured in 1N HCl (20 mL) and extracted twice with EA (20 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvent was removed under reduced pressure to give the title compound as a brown solid along with 2-[5-(2-methyl-[1,3]dioxolan-2-yl)-thiophen-2-ylmethyl]-oxazole-4-carboxylic acid.

Workup

  1. extractionextracted twice with EA (20 mL)
  2. dry with materialextracts were dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9fde04796f5040dc9614d98e3771e782
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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