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Lithium hydroxide, monohydrate → (R)-2-Hydroxy-3-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)propanoic acid

HRID 501934
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HRID 501934 반응식
C([O:4][C@H:5]([CH2:10][C:11]1[CH:19]=[C:18]([CH3:20])[C:17]2[C:13](=[CH:14][N:15]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[N:16]=2)[CH:12]=1)[C:6]([O:8]C)=[O:7])(=O)C.O.[OH-].[Li+]>O1CCCC1.CO.O>[OH:4][C@H:5]([CH2:10][C:11]1[CH:19]=[C:18]([CH3:20])[C:17]2[C:13](=[CH:14][N:15]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:27])([CH3:26])[CH3:28])[N:16]=2)[CH:12]=1)[C:6]([OH:8])=[O:7]
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HCID 168937Lithium hydroxide, monohydrateHCID 59424274(R)-Methyl 2-acetoxy-3-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)propanoate

생성물 1

HCID 59424393(R)-2-Hydroxy-3-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)propanoic acid

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매
HCID 8028
Tetrahydrofuran
용매

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온도
0 °C

실험 절차

To a solution of (R)-methyl 2-acetoxy-3-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)propanoate (700 mg, 1.72 mmol) in tetrahydrofuran (6 mL) and methanol (6 mL) at 0° C. was added a solution of lithium hydroxide monohydrate (289 mg, 6.89 mmol) in water (6 mL). The reaction was stirred at 0° C. for 1 h. The reaction was concentrated, dissolved in 5 mL of water, cooled to 0° C., and treated with 1M hydrochloric acid until mildly acidic. A non-solid ppt formed. The suspension was extracted with ethyl acetate (2×), which were washed with brine, dried over magnesium sulfate, and concentrated to give 620 mg (quant.) which was pure by LC/MS and was used without purification. Mass spec.: 351.13 (MH)+.

후처리

  1. concentrationThe reaction was concentrated
  2. dissolutiondissolved in 5 mL of water
  3. temperaturecooled to 0° C.
  4. additiontreated with 1M hydrochloric acid until mildly acidic
  5. customA non-solid ppt formed
  6. extractionThe suspension was extracted with ethyl acetate (2×), which
  7. washwere washed with brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. customto give 620 mg (quant.) which
  11. customwas used without purification

출처 및 근거

ORD 기록
ord-9af57409fd2c41488c07c1472465fa28
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07772244B2

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