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Water → (R)-3-[4-(3-Amino-benzo[d]isoxazol-6-yl)-2,6-dichloro-benzyl]-1-(4-hydroxy-piperidin-1-yl)-pyrrolidin-2-one

HRID 1692102
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HRID 1692102 반응식
O.C(O)(C(F)(F)F)=O.[NH2:9][C:10]1[C:14]2[CH:15]=[CH:16][C:17]([C:19]3[CH:48]=[C:47]([Cl:49])[C:22]([CH2:23][C@@H:24]4[CH2:28][CH2:27][N:26]([N:29]5[CH2:34][CH2:33][CH:32]([O:35][Si](C(C)C)(C(C)C)C(C)C)[CH2:31][CH2:30]5)[C:25]4=[O:46])=[C:21]([Cl:50])[CH:20]=3)=[CH:18][C:13]=2[O:12][N:11]=1.C(OCC)(=O)C>C1COCC1>[NH2:9][C:10]1[C:14]2[CH:15]=[CH:16][C:17]([C:19]3[CH:48]=[C:47]([Cl:49])[C:22]([CH2:23][C@@H:24]4[CH2:28][CH2:27][N:26]([N:29]5[CH2:34][CH2:33][CH:32]([OH:35])[CH2:31][CH2:30]5)[C:25]4=[O:46])=[C:21]([Cl:50])[CH:20]=3)=[CH:18][C:13]=2[O:12][N:11]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 66905014(R)-3-[4-(3-Amino-benzo[d]isoxazol-6-yl)-2,6-dichloro-benzyl]-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-2-one

생성물 1

HCID 66905316(R)-3-[4-(3-Amino-benzo[d]isoxazol-6-yl)-2,6-dichloro-benzyl]-1-(4-hydroxy-piperidin-1-yl)-pyrrolidin-2-one수율 87%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Add water (3 mL) and TFA (1 mL) to (R)-3-[4-(3-amino-benzo[d]isoxazol-6-yl)-2,6-dichloro-benzyl]-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-2-one (0.095 g) in THF (3 mL). Stir the mixture at room temperature for 5 hours. Dilute the reaction with ethyl acetate, wash with sodium bicarbonate (sat. solution), separate the organic layer, dry over sodium sulfate, filter and concentrate. Purify the residue on silica gel column by using ethyl acetate first, then switch to 5% methanol in dichloromethane to afford 0.062 g (87%) of the desired product as white solid. MS (m/z): 475 (M+).

후처리

  1. additionDilute
  2. washwash with sodium bicarbonate (sat. solution)
  3. customseparate the organic layer
  4. dry with materialdry over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the residue on silica gel column

출처 및 근거

ORD 기록
ord-6c358fdb9992412088210ea9c828186b
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08153807B2

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