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

HRID 342142ノート

反応式

HRID 342142 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6386tert-Butanol溶媒HCID 105532-Methyl-2-butene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c1b9a949f2f14f3cb31c888cba0f0cb1
出典データセット
uspto-grants-1999_01
特許番号
US05856326

反応ノート

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