Water → 4-{[(tert-butoxycarbonyl)(methyl)amino]methyl}tetrahydro-2H-pyran-4-carboxylic acid

HRID 58349Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]1([C:17]([O:19]C)=[O:18])[CH2:16][CH2:15][O:14][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:17]([OH:19])=[O:18])[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1)[CH3:9])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 60 °C

Procedure

Methyl 4-{[(tert-butoxycarbonyl)(methyl)amino]methyl}tetrahydro-2H-pyran-4-carboxylate (2.81 mmol) was dissolved in methanol (7.3 mL) and water (5.9 mL) and treated with 10 M sodium hydroxide (1.40 mL, 14.0 mmol). The solution was heated at 60° C. overnight. The reaction was cooled to room temperature, and volatiles were removed on a rotovap. The remaining solution was diluted with water and washed with ethyl acetate (2 times). The water layer was cooled with an ice bath and then acidified with a mixture of 1 N aqueous HCl (28.1 mL) and saturated sodium chloride (28.1 mL). The product was extracted with ethyl acetate (3 times), and the organic solution was dried over anhydrous sodium sulfate and filtered. Concentration of the organic solution gave the title compound (750 mg, 97% yield) which was used crude in the next step.

Workup

temperatureThe reaction was cooled to room temperature
customvolatiles were removed on a rotovap
additionThe remaining solution was diluted with water
washwashed with ethyl acetate (2 times)
temperatureThe water layer was cooled with an ice bath
additionacidified with a mixture of 1 N aqueous HCl (28.1 mL) and saturated sodium chloride (28.1 mL)
extractionThe product was extracted with ethyl acetate (3 times)
dry with materialthe organic solution was dried over anhydrous sodium sulfate
filtrationfiltered

Sources & evidence

ORD record: ord-3f811d4c91bc44f6b6688335811c67be
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434753B2

Reaction notes

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