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Hydrochloric Acid → (S)-2-(tert-butoxy)-2-(2-(3-chlorophenyl)-7-isopropyl-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetic acid

HRID 472855
ノート
印刷プレビュー

反応式

HRID 472855 の反応式
[C:1]([O:5][C@@H:6]([C:11]1[C:12]([CH3:30])=[N:13][C:14]2[N:15]([N:20]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=3)[CH:22]=2)[C:16]=1[CH:17]([CH3:19])[CH3:18])[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO>[C:1]([O:5][C@@H:6]([C:11]1[C:12]([CH3:30])=[N:13][C:14]2[N:15]([N:20]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=3)[CH:22]=2)[C:16]=1[CH:17]([CH3:19])[CH3:18])[C:7]([OH:9])=[O:8])([CH3:2])([CH3:3])[CH3:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66691616(S)-methyl 2-(tert-butoxy)-2-(2-(3-chlorophenyl)-7-isopropyl-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate

生成物 1

HCID 66693671(S)-2-(tert-butoxy)-2-(2-(3-chlorophenyl)-7-isopropyl-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetic acid収率 94%

試薬・触媒・溶媒 1

HCID 887
Methanol
溶媒

実験手順

A solution of (S)-methyl 2-(tert-butoxy)-2-(2-(3-chlorophenyl)-7-isopropyl-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (0.060 g, 0.140 mmol) and 1M NaOH (1 ml, 1.000 mmol) in MeOH (5 mL) was heated at 60° C. for 16 h. Then, the reaction mixture was cooled, neutralized with 1M HCl (1 mL), concentrated and the residue was diluted with Et2O (25 mL), washed with 0.1M NH4OAc (5 mL), brine (5 mL), dried (Na2SO4), filtered and concentrated to give (S)-2-(tert-butoxy)-2-(2-(3-chlorophenyl)-7-isopropyl-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetic acid (0.055 g, 0.131 mmol, 94% yield) as white solid and 98% ee. 1H NMR (500 MHz, CDCl3) δ: 7.96 (s, 1H), 7.83 (d, J=7.0 Hz, 1H), 7.39-7.30 (m, 2H), 6.81 (s, 1H), 5.46 (br. s., 1H), 3.99 (br. s., 1H), 2.74 (br. s., 3H), 1.69 (d, J=6.4 Hz, 3H), 1.57 (br. s., 3H), 1.27 (s, 9H). LCMS (M+H) calcd for C22H27ClN3O3: 416.17. found: 416.3.

後処理

  1. temperatureThen, the reaction mixture was cooled
  2. concentrationconcentrated
  3. additionthe residue was diluted with Et2O (25 mL)
  4. washwashed with 0.1M NH4OAc (5 mL), brine (5 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-4847fdd8abb8492ba73df2ec7d833413
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08633200B2

反応ノート

読み込み中…

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