Ethyl Acetate → (S)-4-(tert-butoxycarbonyl)-5-(carboxymethyl)-1-(3-chlorophenyl)piperazin-2-one

HRID 342142Notes

Reaction equation

HRID 342142 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:13]([CH2:14][CH:15]=[O:16])[CH2:12][N:11]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[C:10](=[O:24])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl([O-])=[O:26].[Na+].P([O-])(O)(O)=O.[Na+].CCOC(C)=O>CC(O)(C)C.CC(=CC)C.O>[C:1]([O:5][C:6]([N:8]1[C@@H:13]([CH2:14][C:15]([OH:26])=[O:16])[CH2:12][N:11]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[C:10](=[O:24])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 88302437(S)-4-(tert-butoxycarbonyl)-1-(3-chlorophenyl)-5-[2-(oxo)ethyl]piperazin-2-one

Product 1

HCID 53926412(S)-4-(tert-butoxycarbonyl)-5-(carboxymethyl)-1-(3-chlorophenyl)piperazin-2-one

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 105532-Methyl-2-buteneSolvent

Procedure

To a solution of the aldehyde from Step A (1.52 g, 4.31 mmol) in 2-methyl-2-propanol (50 mL) and 2-methyl-2-butene (10 mL) at room temperature was added a solution of sodium chlorite (585 mg, 5.17 mmol) and sodium dihydrogenphosphate (595 mg, 4.31 mmol) in 10 mL of water. The reaction turned yellow, then slowly faded to light pink over 45 minutes. The solution was poured into EtOAc, and washed with sat. sodium bisulfite soln. The aqueous layer was acidified to pH 3 with 2.75M KHSO4 soln., and extracted several times with EtOAc. The combined organic extracts were dried (Na2SO4), filtered, and concentrated in vacuo to provide the titled carboxylic acid.

Workup

  1. washwashed with sat. sodium bisulfite soln
  2. extraction, and extracted several times with EtOAc
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c1b9a949f2f14f3cb31c888cba0f0cb1
Source dataset
uspto-grants-1999_01
Patent number
US05856326

Reaction notes

Loading…