Hydrochloric Acid → HCID 54212501, compound

HRID 544263Notes

Reaction equation

HRID 544263 reaction equation
C(O[C@H:5]1[C@H:10]2[C@H:8]([C:9]2([CH3:12])[CH3:11])[C:7](=[O:13])[O:6]1)(=O)C.Cl.[CH3:15][O:16][NH2:17].[OH-].[Na+].Cl>C(O)C>[CH3:12][C:9]1([CH3:11])[C@@H:10]([CH:5]=[N:17][O:16][CH3:15])[C@H:8]1[C:7]([OH:6])=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 521874O-Methylhydroxylamine hydrochlorideHCID 13228611HCID 13228611, compound

Product 1

HCID 54212501HCID 54212501, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 184 mg sample of (1R,4R,5S)-4-acetoxy-6,6-dimethyl-3-oxabicyclo[3.1.0]hexane-2-one in 2.5 ml of 60% aqueous ethanol was treated with 835 mg of methoxyamine hydrochloride and 40 mg of sodium hydroxide at room temperature. After 4 hours, the resulting mixture was acidified to pH 2 with dilute hydrochloric acid, and extracted with methylene chloride. The organic phase was dried (MgSO4) and stripped to yield 148 mg of the desired (1R,cis)-2,2-dimethyl-3-((methoxyimino)methyl)cyclopropanecarboxylic acid.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe organic phase was dried (MgSO4)

Sources & evidence

ORD record
ord-e39243d2403a49909ce61e32ff104f46
Source dataset
uspto-grants-1984_05
Patent number
US04448986

Reaction notes

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