Potassium Sodium Tartrate → HCID 14014843, compound

HRID 2180224Notes

Reaction equation

HRID 2180224 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].COCCO[Al+]OCCOC.[Na+].[H-].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1>[CH:14]1([CH2:13][C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:10][OH:11])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 2755927(2R)-2-{[(tert-butoxy)carbonyl]amino}-3-cyclohexylpropanoic acidHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 14014843HCID 14014843, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (2R)-2-((tert-butoxycarbonyl)amino)-3-cyclohexylpropanoic acid (30.4 g, 112 mmol) in toluene (300 mL) at 0° C. was treated with sodium bis(2-methoxyethoxy)aluminum hydride (Red-Al®) (115 mmol) over 45 minutes. The mixture was stirred for 30 minutes, warmed to room temperature, stirred for 1 hour, treated with aqueous Rochelle salt, and extracted with diethyl ether. The extract was washed with brine and aqueous NaHCO3, dried (MgSO4), filtered, and concentrated to provide the desired product.

Workup

  1. stirringstirred for 1 hour
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with brine and aqueous NaHCO3
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2ae7e44e3aa043be99e8b7bca7f4a3dc
Source dataset
uspto-grants-2005_05
Patent number
US06887863B2

Reaction notes

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