Sulfuric Acid → HCID 58765776, compound

HRID 860654Notes

Reaction equation

HRID 860654 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH:5]([NH:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1)[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:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=2)[O:18][C:6]=1[CH3:7]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 69357651HCID 69357651, compound

Product 1

HCID 58765776HCID 58765776, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
40 °C

Procedure

3-(4-Bromo-benzoylamino)-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 then concentrated to dryness and purified by column chromatography. This procedure yielded (11.6 g, 37.4 mmol) 48.3% of the desired oxazole.

Workup

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

Sources & evidence

ORD record
ord-6393edafbed14cf1a097a9b85bf54e88
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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