Sodium Hydroxide → N-[4-(3-tert-butoxy-2,2-dimethyl-3-oxopropyl)benzyl]-N-(2-furylmethyl)glycine

HRID 353170Notes

Reaction equation

C([O:3][C:4](=[O:31])[CH2:5][N:6]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([CH3:30])([CH3:29])[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:16][CH:15]=1)[CH2:7][C:8]1[O:9][CH:10]=[CH:11][CH:12]=1)C.[OH-].[Na+]>C(O)C>[C:25]([O:24][C:22](=[O:23])[C:21]([CH3:30])([CH3:29])[CH2:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:6]([CH2:7][C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[CH2:5][C:4]([OH:31])=[O:3])=[CH:15][CH:16]=1)([CH3:28])([CH3:26])[CH3:27]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 785 mg (1.83 mmol) of tert-butyl 3-(4-{[(2-ethoxy-2-oxoethyl)(2-furylmethyl)amino]methyl}phenyl)-2,2-dimethylpropionate (Example I-9) in 15 ml of ethanol is admixed with 5.5 ml (5.5 mmol) of 1 N aqueous sodium hydroxide solution and heated at 80° C. for 1 h. After cooling, the mixture is concentrated under reduced pressure and the residue is taken up in a little water, acidified with 1 N hydrochloric acid and extracted 3× with ethyl acetate. The combined organic extracts are washed 2× with sat. NaCl solution, dried over sodium sulphate and freed from the solvent under reduced pressure. This gives 728 mg (99%) of N-[4-(3-tert-butoxy-2,2-dimethyl-3-oxopropyl)benzyl]-N-(2-furylmethyl)glycine.

Workup

temperatureAfter cooling
concentrationthe mixture is concentrated under reduced pressure
extractionextracted 3× with ethyl acetate
washThe combined organic extracts are washed 2× with sat. NaCl solution
dry with materialdried over sodium sulphate

Sources & evidence

ORD record: ord-f6edc8b7ce244dc4b94b55672bbeb416
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06750236B2

Reaction notes

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