Sodium Hydroxide → HCID 86722942, compound

HRID 1404333Notes

Reaction equation

HRID 1404333 reaction equation
C([O:3][C:4](=[O:21])[CH:5]=[C:6]1[CH2:11][CH2:10][CH:9]([CH2:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:8][CH2:7]1)C.[OH-].[Na+]>CO.C1COCC1>[C:17]([O:16][C:14]([NH:13][CH2:12][CH:9]1[CH2:8][CH2:7][C:6](=[CH:5][C:4]([OH:21])=[O:3])[CH2:11][CH2:10]1)=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86722941HCID 86722941, compound

Product 1

HCID 86722942HCID 86722942, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [4-(tert-Butoxycarbonylamino-methyl)-cyclohexylidene]-acetic acid ethyl ester (0.518 g, 1.74 mmol) in MeOH (16 mL) and THF (4 mL) was added sodium hydroxide (9.0 mL, 1N, 9.0 mmol) and the reaction stirred at RT for 23 hr. The reaction was quenched with H2O and extracted with EtOAc (2×). The aqueous layer was acidified to pH ˜1 with 1N HCl and extracted with EtOAc (3×). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to provide 0.300 g (64%) of product. ESI-MS m/z 270 (MH)+.

Workup

  1. customThe reaction was quenched with H2O
  2. extractionextracted with EtOAc (2×)
  3. extractionextracted with EtOAc (3×)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-47603aa9eda6462d975ba68aeccde7d8
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

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