Sulfuric Acid → 2,2-Dimethyl-3-[4-({[(2'-oxospiro[cyclopentane-1,3'-indol]-1'(2'H)-yl)carbonyl]amino}methyl)piperidin-1-yl]propanoic acid

HRID 733088

反応式

HRID 733088 の反応式
[CH3:1][C:2]([CH3:32])([CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]([N:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]3([CH2:30][CH2:29][CH2:28][CH2:27]3)[C:19]2=[O:31])=[O:17])[CH2:10][CH2:9]1)[C:3]([O:5]C)=[O:4].OS(O)(=O)=O.C([O-])(O)=O.[Na+].C(Cl)Cl>C(O)(=O)C.O>[CH3:1][C:2]([CH3:32])([CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]([N:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]3([CH2:30][CH2:29][CH2:28][CH2:27]3)[C:19]2=[O:31])=[O:17])[CH2:10][CH2:9]1)[C:3]([OH:5])=[O:4]

参加物

7

反応物 4

HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 67232986Methyl 2,2-dimethyl-3-[4-({[(2'-oxospiro[cyclopentane-1,3'-indol]-1'(2'H)-yl)carbonyl]amino}methyl)piperidin-1-yl]propanoate

生成物 1

HCID 119979742,2-Dimethyl-3-[4-({[(2'-oxospiro[cyclopentane-1,3'-indol]-1'(2'H)-yl)carbonyl]amino}methyl)piperidin-1-yl]propanoic acid収率 80%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

実験手順

To a stirred solution of methyl 2,2-dimethyl-3-[4-({[(2′-oxospiro[cyclopentane-1,3′-indol]-1′(2′H)-yl)carbonyl]amino}methyl)piperidin-1-yl]propanoate (170 mg, 0.38 mmol, step 3 of Example 2) in acetic acid (2 mL), H2SO4 (113 mg) in water (2 mL) was added, and the mixture was refluxed for 36 h. The mixture was cooled to room temperature and solid NaHCO3 (500 mg) was added slowly. The resulting mixture was concentrated to give white solid. To the solid, CH2Cl2 (40 mL) was added and stirred for 10 min, dried over MgSO4. The solution was filtered and concentrated and then resulted yellow oil. The oil was chromatographed on a column of silica gel eluting with CH2Cl2/methanol (14:1) to give 130 mg (80%) of the title compound as white solid. Recrystallization from ethyl acetate/diethyl ether gave white powder.

後処理

  1. temperaturethe mixture was refluxed for 36 h
  2. concentrationThe resulting mixture was concentrated
  3. customto give white solid
  4. dry with materialdried over MgSO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated
  7. customresulted yellow oil
  8. customThe oil was chromatographed on a column of silica gel eluting with CH2Cl2/methanol (14:1)

出典と根拠

ORDレコード
ord-6589e84a55e74305a6452d210621256f
出典データセット
uspto-grants-2009_09
特許番号
US07589109B2

関連ノート

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