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

HRID 342142노트

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HRID 342142 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6386tert-Butanol용매HCID 105532-Methyl-2-butene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c1b9a949f2f14f3cb31c888cba0f0cb1
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05856326

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