HCID 23204313, compound → HCID 23204319, compound

HRID 322880Notes

Reaction equation

HRID 322880 reaction equation
[C:1]([C:4]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:21][C:5]=1[O:6][CH:7]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(=O)[NH2:2]>C(OC(=O)C)(=O)C>[C:1]([C:4]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:21][C:5]=1[O:6][CH:7]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])#[N:2]

Participants

3

Reactant 1

HCID 23204313HCID 23204313, compound

Product 1

HCID 23204319HCID 23204319, compoundYield 32.9%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of ethyl (RS)-4-(2-carbamoyl-5-benzyloxyphenoxy)-4-phenylbutanoate (1.9 g) and acetic anhydride (50 mL) is stirred at reflux for 2 hours. The reaction mixture is evaporated to low bulk and the residue is dissolved in ethyl acetate (50 mL). This solution is washed with aqueous sodium hydrogen carbonate and water, dried, and evaporated. Flash chromatography, eluting with a mixture of cyclohexane and dichloromethane (15:85 v/v), gives ethyl (RS)-4-(2-cyano-5-benzyloxyphenoxy)-4-phenylbutanoate (0.6 g).

Workup

  1. temperatureat reflux for 2 hours
  2. customThe reaction mixture is evaporated to low bulk
  3. dissolutionthe residue is dissolved in ethyl acetate (50 mL)
  4. washThis solution is washed with aqueous sodium hydrogen carbonate and water
  5. customdried
  6. customevaporated
  7. washFlash chromatography, eluting with a mixture of cyclohexane and dichloromethane (15:85 v/v)

Sources & evidence

ORD record
ord-d1ea8174eed043f5aa1a702fcb590dcd
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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