Methanesulfonic Acid → (3R)-3-(2,6-Dichloro-4-hydroxy-benzyl)-1-(4,5,6,7-tetrahydro-1H-indazol-6-yl)-pyrrolidin-2-one

HRID 1013823노트

반응식

HRID 1013823 반응식
C([O:8][C:9]1[CH:30]=[C:29]([Cl:31])[C:12]([CH2:13][C@@H:14]2[CH2:18][CH2:17][N:16]([CH:19]3[CH2:27][C:26]4[NH:25][N:24]=[CH:23][C:22]=4[CH2:21][CH2:20]3)[C:15]2=[O:28])=[C:11]([Cl:32])[CH:10]=1)C1C=CC=CC=1.CS(O)(=O)=O>CSC>[Cl:32][C:11]1[CH:10]=[C:9]([OH:8])[CH:30]=[C:29]([Cl:31])[C:12]=1[CH2:13][C@@H:14]1[CH2:18][CH2:17][N:16]([CH:19]2[CH2:27][C:26]3[NH:25][N:24]=[CH:23][C:22]=3[CH2:21][CH2:20]2)[C:15]1=[O:28]

참가 물질

4

반응물 2

HCID 6395Methanesulfonic AcidHCID 67317121(3R)-3-(4-Benzyloxy-2,6-dichloro-benzyl)-1-(4,5,6,7-tetrahydro-1H-indazol-6-yl)-pyrrolidin-2-one

생성물 1

HCID 67316410(3R)-3-(2,6-Dichloro-4-hydroxy-benzyl)-1-(4,5,6,7-tetrahydro-1H-indazol-6-yl)-pyrrolidin-2-one수율 113.2%

시약·촉매·용매 1

HCID 1068Dimethyl Sulfide용매

실험 절차

To a solution of (3R)-3-(4-benzyloxy-2,6-dichloro-benzyl)-1-(4,5,6,7-tetrahydro-1H-indazol-6-yl)-pyrrolidin-2-one (3.93 g, 8.36 mmol) in dimethylsulfide (45 mL), add methane sulfonic acid (13.23 g, 138 mmol) and stir the mixture vigorously under nitrogen atmosphere at room temperature for 18 hours. Remove the solvent in vacuo and dilute the residue with water, adjust the pH to pH=7 with 5 N NaOH, and extract the mixture several times with ethyl acetate and THF. After drying the combined organic layer (Na2SO4), filter and concentrate under vacuum to afford 3.60 g (100%) of the title compound. MS (m/z): 381 (M+).

후처리

  1. customRemove the solvent in vacuo
  2. additiondilute the residue with water
  3. extractionextract the mixture several times with ethyl acetate and THF
  4. dry with materialAfter drying the combined organic layer (Na2SO4)
  5. filtrationfilter
  6. concentrationconcentrate under vacuum

출처 및 근거

ORD 기록
ord-189297764f9c4b8c93027942d8f3fb8c
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981918B2

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