Sodium Hydroxide → Mk-8245

HRID 561212ノート

反応式

HRID 561212 の反応式
[Br:1][C:2]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:15]=[C:14]([C:16]3[N:17]=[N:18][N:19]([CH2:21][C:22]([O:24]CC)=[O:23])[N:20]=3)[O:13][N:12]=2)[CH2:7][CH2:6]1.[OH-].[Na+]>C1COCC1.CO>[Br:1][C:2]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:15]=[C:14]([C:16]3[N:17]=[N:18][N:19]([CH2:21][C:22]([OH:24])=[O:23])[N:20]=3)[O:13][N:12]=2)[CH2:7][CH2:6]1

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 53388532Ethyl (5-{3-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]isoxazol-5-yl}-2H-tetrazol-2-yl)acetate

生成物 1

HCID 24988881Mk-8245

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of ethyl (5-{3-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]isoxazol-5-yl}-2H-tetrazol-2-yl)acetate (1.3 g, 2.62 mmol) in THF (15 mL) and MeOH (5 mL) was added 1M sodium hydroxide (5.25 mL, 5.25 mmol). The mixture was stirred at room temperature for 1 h. Volatile solvents were removed in vacuo. The residue was diluted with water (20 mL), acidified with 1M HCl (6 mL) and extracted with EtOAc. The EtOAc extract was washed with water, dried (Na2SO4) and concentrated. The residue was triturated with diethyl ether to give the crude product, containing about 5% of the 1-isomer. Further purification by trituration in isopropyl acetate (2×, 80° C. overnight, then room temperature overnight) provided the title compound as a beige powder.

後処理

  1. customVolatile solvents were removed in vacuo
  2. additionThe residue was diluted with water (20 mL)
  3. extractionextracted with EtOAc
  4. extractionThe EtOAc extract
  5. washwas washed with water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was triturated with diethyl ether
  9. customto give the crude product
  10. customFurther purification by trituration in isopropyl acetate (2×, 80° C. overnight

出典と根拠

ORDレコード
ord-c0732cf615164cf896a991687af1f34e
出典データセット
uspto-grants-2011_11
特許番号
US08063224B2

反応ノート

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