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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 2235919
ノート
印刷プレビュー

反応式

HRID 2235919 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962
Water
溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-f991d80486964041834ba79b66596c33
出典データセット
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07714004B2

反応ノート

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