Sodium Hydroxide → 2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-1-yl)butanoic acid

HRID 932122ノート

反応式

HRID 932122 の反応式
[CH2:1]([C@@:4]1([CH3:32])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:6]([C@@H:24]([CH2:29][CH3:30])[C:25]([O:27]C)=[O:26])[C:5]1=[O:31])[CH:2]=[CH2:3].[OH-].[Na+]>C1COCC1.O>[CH2:1]([C@@:4]1([CH3:32])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)[N:6]([CH:24]([CH2:29][CH3:30])[C:25]([OH:27])=[O:26])[C:5]1=[O:31])[CH:2]=[CH2:3]

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 58573915(S)-Methyl 2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-1-yl)butanoate

生成物 1

HCID 585735702-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-1-yl)butanoic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of methyl 2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-1-yl)butanoate (200 mg, 0.42 mmol; Example 91, Step A) in THF (5 mL) was added sodium hydroxide (506 mg, 12.65 mmol) in water (5 mL) and the reaction was heated at reflux for about 12 h. After this time the reaction was cooled to rt and partitioned between EtOAc (80 mL) and 1.0 M HCl (20 mL). The separated aqueous layer was extracted with EtOAc (30 mL) and the combined organic layers were dried over MgSO4, filtered and the filtrate was evaporated in vacuo to give the title compound as a white solid.

後処理

  1. temperaturethe reaction was heated
  2. temperatureat reflux for about 12 h
  3. custompartitioned between EtOAc (80 mL) and 1.0 M HCl (20 mL)
  4. extractionThe separated aqueous layer was extracted with EtOAc (30 mL)
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. customthe filtrate was evaporated in vacuo

出典と根拠

ORDレコード
ord-88e711c8e2f94743a2941ff642e6d7e1
出典データセット
uspto-grants-2016_03
特許番号
US09296736B2

反応ノート

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