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Hydrochloric Acid → [2-fluoro-4-(2-{(1S,2R)-2-{1-[5-(methoxymethyl)pyrimidin-2-yl]piperidin-4-yl}cyclopropyl}ethoxy)phenyl]acetic acid

HRID 1474697
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HRID 1474697 반응식
C[O:2][C:3](=[O:33])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][C@@H:14]2[CH2:16][C@@H:15]2[CH:17]2[CH2:22][CH2:21][N:20]([C:23]3[N:28]=[CH:27][C:26]([CH2:29][O:30][CH3:31])=[CH:25][N:24]=3)[CH2:19][CH2:18]2)=[CH:7][C:6]=1[F:32].CO.[OH-].[Li+].Cl>O1CCCC1.O>[F:32][C:6]1[CH:7]=[C:8]([O:11][CH2:12][CH2:13][C@@H:14]2[CH2:16][C@@H:15]2[CH:17]2[CH2:22][CH2:21][N:20]([C:23]3[N:24]=[CH:25][C:26]([CH2:29][O:30][CH3:31])=[CH:27][N:28]=3)[CH2:19][CH2:18]2)[CH:9]=[CH:10][C:5]=1[CH2:4][C:3]([OH:33])=[O:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 89583790Methyl{2-fluoro-4-[2-((1S,2R)-2-{1-[5-(methoxymethyl)pyrimidin-2-yl]piperidin-4-yl}cyclopropyl)ethoxy]phenyl}acetate

생성물 1

HCID 117678258[2-fluoro-4-(2-{(1S,2R)-2-{1-[5-(methoxymethyl)pyrimidin-2-yl]piperidin-4-yl}cyclopropyl}ethoxy)phenyl]acetic acid

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of methyl{2-fluoro-4-[2-((1S,2R)-2-{1-[5-(methoxymethyl)pyrimidin-2-yl]piperidin-4-yl}cyclopropyl)ethoxy]phenyl}acetate (1.50 g, 3.28 mmol) in 21 ml of tetrahydrofuran was added 14 ml of methanol and 14 ml of water. Lithium hydroxide (0.393 g, 16.4 mmol) was added to the mixture, and stirred at RT overnight. 1 M hydrochloric acid was added to adjust the pH to 4. The volatiles were removed in vacuo, and the remaining aqueous layer extracted with dichloromethane (3×30 ml). The organic fractions were combined, dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (50 g silica gel) using a gradient eluent of 0-70% ethyl acetate in hexanes (1000 ml) to afford the title compound. LC/MS (m/z) 444.4 (M+H)+.

후처리

  1. customThe volatiles were removed in vacuo
  2. extractionthe remaining aqueous layer extracted with dichloromethane (3×30 ml)
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (50 g silica gel)

출처 및 근거

ORD 기록
ord-96edfffa047c4de38f87f02601228922
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09018224B2

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