HCID 21968740, compound → HCID 21968739, compound

HRID 1108324Notes

Reaction equation

HRID 1108324 reaction equation
C([O:5][C:6]([CH2:8][CH:9]([CH2:22][CH:23]1[CH2:26][CH2:25][CH2:24]1)[C:10]([NH:12][C@H:13]([C:18]([NH:20][CH3:21])=[O:19])[C:14]([CH3:17])([CH3:16])[CH3:15])=[O:11])=[O:7])(C)(C)C>FC(F)(F)C(O)=O>[C:6]([CH2:8][CH:9]([CH2:22][CH:23]1[CH2:24][CH2:25][CH2:26]1)[C:10]([NH:12][C@H:13]([C:18]([NH:20][CH3:21])=[O:19])[C:14]([CH3:17])([CH3:16])[CH3:15])=[O:11])([OH:7])=[O:5]

Participants

3

Reactant 1

HCID 21968740HCID 21968740, compound

Product 1

HCID 21968739HCID 21968739, compoundYield 103.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1.37 g of N2[2(RS)[tert-butoxycarbonylmethyl]-3-cyclobutylpropionyl]-N1,3-dimethyl-L-valinamide as a 1:1 mixture of diastereoisomers in 20 ml of trifluoroacetic acid was stirred at room temperature for 2.5 hours. The solvent was removed by evaporation to leave an oil which was partitioned between diethyl ether and 5% sodium hydrogen carbonate solution. The aqueous phase was acidified with hydrochloric acid and extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulphate and then evaporated to give 1.2 g of N2-[2(RS)[carboxymethyl]-3-cyclobutylpropionyl]-N1,3-dimethyl-L-valinamide as a 1:1 mixture of diastereoisomers in the form of a white foam.

Workup

  1. customThe solvent was removed by evaporation
  2. customto leave an oil which
  3. customwas partitioned between diethyl ether and 5% sodium hydrogen carbonate solution
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-7eb1f8e3223d408685c929a58179ea2d
Source dataset
uspto-grants-2000_05
Patent number
US06066662

Reaction notes

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