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Methanol → (4-{2-[(1S,2R)-2-{1-[5-(ethoxymethyl)pyrimidin-2-yl]piperidin-4-yl}cyclopropyl]ethoxy}-2-fluorophenyl)acetic acid

HRID 1474705
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HRID 1474705 반응식
[CH2:1]([O:3][CH2:4][C:5]1[CH:6]=[N:7][C:8]([N:11]2[CH2:16][CH2:15][CH:14]([C@H:17]3[CH2:19][C@H:18]3[CH2:20][CH2:21][O:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][C:30]([O:32]C)=[O:31])=[C:25]([F:34])[CH:24]=3)[CH2:13][CH2:12]2)=[N:9][CH:10]=1)[CH3:2].CO.[OH-].[Li+]>C1COCC1>[CH2:1]([O:3][CH2:4][C:5]1[CH:6]=[N:7][C:8]([N:11]2[CH2:12][CH2:13][CH:14]([C@H:17]3[CH2:19][C@H:18]3[CH2:20][CH2:21][O:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][C:30]([OH:32])=[O:31])=[C:25]([F:34])[CH:24]=3)[CH2:15][CH2:16]2)=[N:9][CH:10]=1)[CH3:2]
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HCID 887MethanolHCID 3939Lithium HydroxideHCID 89583896Methyl (4-{2-[(1S,2R)-2-{1-[5-(ethoxymethyl)pyrimidin-2-yl]piperidin-4-yl}cyclopropyl]ethoxy}-2-fluorophenyl)acetate

생성물 1

HCID 89582003(4-{2-[(1S,2R)-2-{1-[5-(ethoxymethyl)pyrimidin-2-yl]piperidin-4-yl}cyclopropyl]ethoxy}-2-fluorophenyl)acetic acid

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

Methyl (4-{2-[(1S,2R)-2-{1-[5-(ethoxymethyl)pyrimidin-2-yl]piperidin-4-yl}cyclopropyl]ethoxy}-2-fluorophenyl)acetate (1.4 g, 2.97 mmol) was dissolved in THF (3 ml):MeOH (30 ml) and 1M lithium hydroxide (14.84 ml, 14.84 mmol) added. The mixture was stirred at RT overnight. The mixture was concentrated in vacuo and the residue diluted with water (5 mL). The pH of the solution was adjusted to pH˜5 by addition of 1N HCl and the aqueous phase was extracted with EtOAc (3×10 mL). The organic fractions were combined, washed with brine, dried over MgSO4 and concentrated under reduced pressure to afford the title compound. LC/MS (m/z): 458 (M+H)+.

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthe residue diluted with water (5 mL)
  3. additionThe pH of the solution was adjusted to pH˜5 by addition of 1N HCl
  4. extractionthe aqueous phase was extracted with EtOAc (3×10 mL)
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-894090eea6d44192ae50201907d83998
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09018224B2

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