ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Sodium Hydroxide → (5-(Cyano-dimethyl-methyl)-2-{3-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-phenyl}-2H-pyrazol-3-yl)-carbamic acid 2,2,2-trichloro-ethyl ester

HRID 2200051
ノート
印刷プレビュー

反応式

HRID 2200051 の反応式
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][CH2:15][O:16][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)[CH:8]=2)[N:5]=[C:4]([C:23]([CH3:27])([CH3:26])[C:24]#[N:25])[CH:3]=1.[OH-].[Na+].Cl[C:31]([O:33][CH2:34][C:35]([Cl:38])([Cl:37])[Cl:36])=[O:32]>CCOC(C)=O>[Cl:36][C:35]([Cl:38])([Cl:37])[CH2:34][O:33][C:31](=[O:32])[NH:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][CH2:15][O:16][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)[CH:8]=2)[N:5]=[C:4]([C:23]([C:24]#[N:25])([CH3:27])[CH3:26])[CH:3]=1
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 14798Sodium HydroxideHCID 870632,2,2-Trichloroethyl chloroformate3 回HCID 1177287572-(5-Amino-1-{3-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-phenyl}-1H-pyrazol-3-yl)-2-methyl-propionitrile

生成物 1

HCID 117729108(5-(Cyano-dimethyl-methyl)-2-{3-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-phenyl}-2H-pyrazol-3-yl)-carbamic acid 2,2,2-trichloro-ethyl ester収率 80%

試薬・触媒・溶媒 1

HCID 8857
Ethyl Acetate
溶媒

実験手順

Intermediate 20c (317 mg, 0.86 mmol) was dissolved in EtOAc (2.5 mL) and 1M NaOH solution (1.4 mL, 2.14 mmol) and cooled in an ice bath. While stirring, 2,2,2-trichloroethyl chloroformate (227 mg, μL, 1.07 mmol) was then added dropwise, and the ice bath removed. After 30 min, a further 0.65 eq. of 2,2,2-trichloroethyl chloroformate was added, and the reaction continued. After 30 min, a further 0.65 eq. of 2,2,2-trichloroethyl chloroformate was added, and the reaction continued overnight. The reaction was then partitioned between H2O and EtOAc, the organic layer was separated, and the aqueous layer extracted again with EtOAc. The combined organics were dried over MgSO4, concentrated in vacuo and subjected to FCC, eluting with 5-30% EtOAc in cyclohexane, to afford the title compound as a light yellow oil (375 mg, 80%). LCMS (Method 3): Rt 4.41 min, m/z 567, 569 [M+Na].

後処理

  1. customthe ice bath removed
  2. waitAfter 30 min
  3. customthe reaction continued overnight
  4. customThe reaction was then partitioned between H2O and EtOAc
  5. customthe organic layer was separated
  6. extractionthe aqueous layer extracted again with EtOAc
  7. dry with materialThe combined organics were dried over MgSO4
  8. concentrationconcentrated in vacuo
  9. washeluting with 5-30% EtOAc in cyclohexane

出典と根拠

ORDレコード
ord-9876eb4da6cd4002b81635d1c1cc20b6
出典データセット
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09359354B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート