Sodium hydride → HCID 178486046, compound

HRID 1519210Notes

Reaction equation

HRID 1519210 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][C@@H:11]1[CH2:16][CH2:15][C@H:14]([C:17]([OH:19])=[O:18])[CH2:13][CH2:12]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:20]N(C)C(=O)C>>[C:3]([O:7][C:8]([N:10]([CH3:20])[C@@H:11]1[CH2:12][CH2:13][C@H:14]([C:17]([OH:19])=[O:18])[CH2:15][CH2:16]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 31374DimethylacetamideHCID 178453971HCID 178453971, compound

Product 1

HCID 178486046HCID 178486046, compound

Procedure

Sodium hydride (0.22 g) is added to a solution of cis-4-tert-butoxycarbonylamino-cyclohexanecarboxylic acid (0.49 g) in N,N-dimethylacetamide (5 mL) chilled in an ice bath. The cooling bath is removed and the mixture is stirred at room temperature for 1.5 h. Then, the mixture is cooled in an ice bath and methyl iodide (0.63 mL) is added. The cooling bath is removed and the mixture is stirred at room temperature overnight. 1 M aqueous NaOH solution (6 mL) is added and the mixture is stirred at room temperature for another 12 h. Then diethyl ether is added and the aqueous phase is separated. The organic phase is extracted three times with water and the aqueous extracts and phase are combined and acidified using 2 M aqueous KHSO4 solution. The acidic aqueous phase is extracted with diethyl ether and the combined organic extracts are dried (Na2SO4). The solvent is evaporated to afford the title compound as a solid.

Workup

  1. temperaturechilled in an ice bath
  2. customThe cooling bath is removed
  3. temperatureThen, the mixture is cooled in an ice bath
  4. additionmethyl iodide (0.63 mL) is added
  5. customThe cooling bath is removed
  6. stirringthe mixture is stirred at room temperature overnight
  7. addition1 M aqueous NaOH solution (6 mL) is added
  8. stirringthe mixture is stirred at room temperature for another 12 h
  9. additionThen diethyl ether is added
  10. customthe aqueous phase is separated
  11. extractionThe organic phase is extracted three times with water
  12. extractionThe acidic aqueous phase is extracted with diethyl ether
  13. dry with materialthe combined organic extracts are dried (Na2SO4)
  14. customThe solvent is evaporated

Sources & evidence

ORD record
ord-0e83a35d8b014ea9944468c071668fb0
Source dataset
uspto-grants-2015_07
Patent number
US09073870B2

Reaction notes

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