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Lithium hydroxide, monohydrate → HCID 86628124, 화합물

HRID 2190332
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HRID 2190332 반응식
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11](=[O:37])[N:12]([C@H:28]1[CH2:32][CH2:31][C@H:30]([C:33]([O:35]C)=[O:34])[CH2:29]1)[CH2:13][CH2:14][CH:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O.[OH-].[Li+]>CO.O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11](=[O:37])[N:12]([C@H:28]1[CH2:32][CH2:31][C@H:30]([C:33]([OH:35])=[O:34])[CH2:29]1)[CH2:13][CH2:14][CH:15]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 86628125HCID 86628125, 화합물

생성물 1

HCID 86628124HCID 86628124, 화합물

시약·촉매·용매 1

HCID 22242641Methanol--water (1/1)용매

반응 조건

온도
55 °C

실험 절차

To a solution of (1S,3S)-methyl 3-(3-(benzo[d]thiazol-2-yl)-1-(3,3-diphenylpropyl)ureido)cyclopentanecarboxylate 42 (303 mg, 589 μmol) in 8:1 MeOH/H2O (18 ml) was added lithium hydroxide hydrate (49.5 mg, 1180 μmol). The reaction mixture was stirred for overnight at 55° C. Volatiles were removed by concentration under reduced pressure. The leftover residue was treated with 10 mL water and 10 mL of aqueous 10% HCl. A precipitate formed upon addition of the acid. After standing for 10 min the precipitate was filtered and washed with copious of amounts of water. After drying under vacuum, the precipitate was purified by injection as a solution in DMF on a reverse phase HPLC column using 5->95% CH3CN/0.1% aqueous TFA as eluant. Product 43 was isolated as white solid (250 mg). LCMS (ES) calcd for C29H29N3O3S 499.2 found 500.2 (MH+).

후처리

  1. customVolatiles were removed by concentration under reduced pressure
  2. additionThe leftover residue was treated with 10 mL water and 10 mL of aqueous 10% HCl
  3. customA precipitate formed upon addition of the acid
  4. waitAfter standing for 10 min
  5. filtrationthe precipitate was filtered
  6. washwashed with copious of amounts of water
  7. customAfter drying under vacuum
  8. customthe precipitate was purified by injection as a solution in DMF on a reverse phase HPLC column

출처 및 근거

ORD 기록
ord-a9a8c8aeff064897a8fccf97354a43cf
출처 데이터셋
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08324396B2

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