Water → 3-Cyano-4-isopropyl-heptanoic acid t-butyl ester

HRID 479076Notes

Reaction equation

COC(=O)[C:4]([C:20]#[N:21])([CH:13]([CH:17]([CH3:19])[CH3:18])[CH2:14][CH2:15][CH3:16])[CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[Na+].[Cl-].O>CS(C)=O.[Cl-].[Na+].O>[C:9]([O:8][C:6](=[O:7])[CH2:5][CH:4]([C:20]#[N:21])[CH:13]([CH:17]([CH3:18])[CH3:19])[CH2:14][CH2:15][CH3:16])([CH3:10])([CH3:12])[CH3:11]

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 2-cyano-2-(1-isopropyl-butyl)-succinic acid 4-tert-butyl ester 1-methyl ester (1.3 g, 4.2 mmol), NaCl (0.25 g, 4.2 mmol), and H2O (0.15 g, 8.3 mmol) in 25 mL of DMSO is warmed to 130° C. for 12 hours. The mixture is cooled to room temperature and diluted with 100 mL of brine. The organic products are extracted into Et2O (3×50 mL). The organic layers are combined and washed with 50 mL of H2O and 50 mL of brine. Drying over Na2SO4 and evaporation of the solvent gives 0.8 g (75% yield) of 3-cyano-4-isopropyl-heptanoic acid t-butyl ester as an oil.

Workup

temperatureThe mixture is cooled to room temperature
extractionThe organic products are extracted into Et2O (3×50 mL)
washwashed with 50 mL of H2O and 50 mL of brine
dry with materialDrying over Na2SO4 and evaporation of the solvent

Sources & evidence

ORD record: ord-eb78a643602b4742a1acc7720cefb73d
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06642398B2

Reaction notes

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