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Lithium Hydroxide → 2-((S)-5-(3-(5-(4,5-dimethylthiazol-2-yl)pyridin-2-yloxy)propoxy)-2,3-dihydro-1H-inden-1-yl)acetic acid

HRID 603451
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HRID 603451 반응식
[CH3:1][C:2]1[N:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]([O:14][CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[C@H:24]([CH2:28][C:29]([O:31]CC)=[O:30])[CH2:23][CH2:22]4)=[N:12][CH:13]=2)[S:5][C:6]=1[CH3:7].[Li+].[OH-]>C1COCC1.CO.O>[CH3:1][C:2]1[N:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]([O:14][CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[C@H:24]([CH2:28][C:29]([OH:31])=[O:30])[CH2:23][CH2:22]4)=[N:12][CH:13]=2)[S:5][C:6]=1[CH3:7]
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참가 물질

6

반응물 2

HCID 3939Lithium HydroxideHCID 59300420ethyl [(1S)-5-(3-{[5-(4,5-dimethyl-1,3-thiazol-2-yl)-2-pyridinyl]oxy}propoxy)-2,3-dihydro-1H-inden-1-yl]acetate

생성물 1

HCID 99805712-((S)-5-(3-(5-(4,5-dimethylthiazol-2-yl)pyridin-2-yloxy)propoxy)-2,3-dihydro-1H-inden-1-yl)acetic acid수율 89.9%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962
Water
용매
HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of ethyl [(1S)-5-(3-{[5-(4,5-dimethyl-1,3-thiazol-2-yl)-2-pyridinyl]oxy}propoxy)-2,3-dihydro-1H-inden-1-yl]acetate (Example 260) (80 mg, 0.17 mmol) in THF (2 mL), methanol (2 mL) and water (1 mL) was added LiOH (40 mg, 1.74 mmol). The reaction mixture was stirred at rt for 18 h, and then concentrated under reduced pressure. The residue was taken up in water and acidified with a 5% aqueous solution of H3PO4, and extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure to give the product (67 mg, 89%). 1H NMR (400 MHz, CD2Cl2) δ 8.57 (d, 1H), 8.06 (dd, 1H), 7.09 (d, 1H), 6.85 (d, 1H), 6.80 (d, 1H), 6.71 (dd, 1H), 4.53 (t, 2H), 4.15 (t, 2H), 3.49 (qt, 1H), 2.92-2.75 (m, 2H), 2.71 (dd, 1H), 2.45-2.28 (m, 8H), 2.32-2.22 (m, 2H), 1.82-1.70 (m, 1H); LC-MS: RT=3.41 min, (M+H)+ 439.0.

후처리

  1. concentrationconcentrated under reduced pressure
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-27fb964539cf40db9e6f6ba0c35a666f
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07906653B2

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