Water → HCID 60034817, compound

HRID 58345Notes

Reaction equation

HRID 58345 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]1([C:14]([O:16]C)=[O:15])[CH2:13][CH2:12]1)[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]1([C:14]([OH:16])=[O:15])[CH2:12][CH2:13]1)[CH3:9])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 117773898HCID 117773898, compound

Product 1

HCID 60034817HCID 60034817, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 1-{[(tert-butoxycarbonyl)(methyl)amino]methyl}cyclopropanecarboxylate was dissolved in methanol (6.8 mL) and water (5.8 mL) and treated with 10M sodium hydroxide (0.98 mL, 9.82 mmol). The solution was heated at 50° C. After 30 minutes, the reaction was cooled with an ice bath and quenched into a cold (ice bath temperature) mixture of 1N hydrogen chloride (19.6 mL) and saturated sodium chloride (19.6 mL). The product was extracted with ethyl acetate (3 times). The organic solution was dried over anhydrous sodium sulfate and filtered. Concentration of the organic solution gave the title compound (680 mg, 94% yield) which was used crude in the next step.

Workup

  1. temperaturethe reaction was cooled with an ice bath
  2. customquenched into a cold (ice bath temperature) mixture of 1N hydrogen chloride (19.6 mL) and saturated sodium chloride (19.6 mL)
  3. extractionThe product was extracted with ethyl acetate (3 times)
  4. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-3360acfd5baa4c48b7ec656857e88f47
Source dataset
uspto-grants-2016_09
Patent number
US09434753B2

Reaction notes

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