Lithium Hydroxide → HCID 22182729, compound

HRID 1297233Notes

Reaction equation

HRID 1297233 reaction equation
C[O:2][C:3]([C:5]1([CH2:11][NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7][CH:6]1[CH:8]([CH3:10])[CH3:9])=[O:4].[Li+].[OH-]>CO.O>[C:16]([O:15][C:13]([NH:12][CH2:11][C:5]1([C:3]([OH:4])=[O:2])[CH2:7][CH:6]1[CH:8]([CH3:9])[CH3:10])=[O:14])([CH3:17])([CH3:19])[CH3:18]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 69516599HCID 69516599, compound

Product 1

HCID 22182729HCID 22182729, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-(tert-butoxycarbonylamino-methyl)-2-isopropyl-cyclopropanecarboxylic acid methyl ester (10.9 g, 40.2 mmol) in MeOH (320 mL) was added a solution of LiOH (4.2 g, 100 mmol) in water (98 mL). The reaction mixture was heated to reflux for 3 hours and cooled to room temperature. Excess of solvent was removed and the residue was dissolved in water (100 mL). The aqueous solution was washed with ether, acidified to pH=3 with 2N HCl and extracted with EtOAc (2×150 mL). The combined organic phase was washed with brine, dried (Na2SO4) and evaporation of the solvent provided 1-(tert-butoxycarbonylamino-methyl)-2-isopropyl-cyclopropanecarboxylic acid (9.0 g, 87%) as a colorless oil: 1H NMR (300 MHz, CD3OD) δ 0.72 (m, 1H), 0.99 (d, J=6.2 Hz, 3H), 1.06 (d, J=6.2 Hz, 3H), 1.28-1.36 (m, 3H), 1.42 (s, 9H), 3.23 (d, J=14.3 Hz, 1H), 3.54 (d, J=14.3 Hz, 1H); 13C NMR (75 MHz, CD3OD) δ 20.0, 23.0, 23.3, 28.8, 30.2, 37.6, 40.8, 80.2, 158.1, 178.5; MS (APCI) m/z258 [M+H]+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. customExcess of solvent was removed
  4. dissolutionthe residue was dissolved in water (100 mL)
  5. washThe aqueous solution was washed with ether
  6. extractionextracted with EtOAc (2×150 mL)
  7. washThe combined organic phase was washed with brine
  8. customdried
  9. custom(Na2SO4) and evaporation of the solvent

Sources & evidence

ORD record
ord-281a3b22271b46aa8a57410f92d9c425
Source dataset
uspto-grants-2007_07
Patent number
US07250433B2

Reaction notes

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