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

반응식

HRID 733088 반응식
[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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6589e84a55e74305a6452d210621256f
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07589109B2

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