Sulfuric Acid → [2-(6-Chloro-pyridin-3-yl)-5-methyl-oxazol-4-yl]-acetic acid methyl ester

HRID 854550

Reaction equation

HRID 854550 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH:5]([NH:9][C:10]([C:12]1[CH:13]=[N:14][C:15]([Cl:18])=[CH:16][CH:17]=1)=[O:11])[C:6](=O)[CH3:7].S(=O)(=O)(O)O>C(OC(=O)C)(=O)C>[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5]1[N:9]=[C:10]([C:12]2[CH:13]=[N:14][C:15]([Cl:18])=[CH:16][CH:17]=2)[O:11][C:6]=1[CH3:7]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 877132023-[(6-Chloro-pyridine-3-carbonyl)-amino]-4-oxo-pentanoic acid methyl ester

Product 1

HCID 58765666[2-(6-Chloro-pyridin-3-yl)-5-methyl-oxazol-4-yl]-acetic acid methyl esterYield 22%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
40 °C

Procedure

3-[(6-Chloro-pyridine-3-carbonyl)-amino]-4-oxo-pentanoic acid methyl ester is dissolved in acetic anhydride (75 mL) and concentrated sulfuric acid is added in 500 uL portions five times over a four hour period. The reaction is monitored by HPLC. The reaction is then heated to 40° C. until the starting material is consumed. The reaction is allowed to proceed at room temperature overnight. The reaction is then concentrated to dryness and purified by column chromatography. This procedure yielded (12.8 g, 48 mmol) 22% of the desired oxazole over four steps.

Workup

  1. customis consumed
  2. concentrationThe reaction is then concentrated to dryness
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-973361e0cb97477593554eef8b429eaa
Source dataset
uspto-grants-2007_08
Patent number
US07259175B2

Linked notes

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