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Lithium hydroxide, monohydrate → HCID 66899051, 화합물

HRID 19399
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HRID 19399 반응식
C[O:2][C:3](=[O:30])[C@@H:4]([N:9]1[CH2:13][C:12]([O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C@H:22]3[CH2:26][O:25][C:24]([CH3:28])([CH3:27])[O:23]3)=[CH:17][CH:16]=2)=[CH:11][C:10]1=[O:29])[CH2:5][CH:6]([CH3:8])[CH3:7].O.[OH-].[Li+]>O1CCCC1.O>[CH3:28][C:24]1([CH3:27])[O:23][C@@H:22]([CH2:21][C:18]2[CH:19]=[CH:20][C:15]([O:14][C:12]3[CH2:13][N:9]([C@@H:4]([CH2:5][CH:6]([CH3:8])[CH3:7])[C:3]([OH:30])=[O:2])[C:10](=[O:29])[CH:11]=3)=[CH:16][CH:17]=2)[CH2:26][O:25]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 66899367HCID 66899367, 화합물

생성물 1

HCID 66899051HCID 66899051, 화합물수율 78%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of (S)-2-{4-[4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-phenoxy]-2-oxo-2,5-dihydro-pyrrol-1-yl}-4-methyl-pentanoic acid methyl ester (0.198 g, 0.47 mmol) in tetrahydrofuran (5 mL) and water (1 mL) was treated with lithium hydroxide monohydrate (0.022 g 0.51 mmol) and stirred at room temperature for 1.5 h. The mixture was partitioned between ethyl acetate and water and the layers separated. The aqueous phase was acidified with 1N aqueous hydrochloric acid (pH=1) and extracted with ethyl acetate. The combined organic layers from extraction of the acidic aqueous layer were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was treated with dichloromethane/hexanes and the precipitate isolated by filtration to afford (S)-2-{4-[4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-phenoxy]-2-oxo-2,5-dihydro-pyrrol-1-yl}-4-methyl-pentanoic acid (148 mg, 77%), as a white solid.

후처리

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customthe layers separated
  3. extractionextracted with ethyl acetate
  4. extractionThe combined organic layers from extraction of the acidic aqueous layer
  5. dry with materialwere dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. additionThe residue was treated with dichloromethane/hexanes
  9. customthe precipitate isolated by filtration

출처 및 근거

ORD 기록
ord-abf790df85d3460f9a32acb2b24d0eeb
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07741327B2

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