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Cesium carbonate → 3-[2-(4-Carboxy-5-trifluoromethyl-furan-2-ylmethoxy)-5-chloro-phenoxy]-azetidine-1-carboxylic acid tert-butyl ester

HRID 237250
ノート
印刷プレビュー

反応式

HRID 237250 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[OH:20])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O:23][C:24]([C:26]1[CH:30]=[C:29]([CH2:31]Br)[O:28][C:27]=1[C:33]([F:36])([F:35])[F:34])=[O:25])C.C([O-])([O-])=O.[Cs+].[Cs+].[OH-].[Na+]>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([O:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[O:20][CH2:31][C:29]2[O:28][C:27]([C:33]([F:35])([F:34])[F:36])=[C:26]([C:24]([OH:25])=[O:23])[CH:30]=2)[CH2:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 13237850Ethyl 5-(bromomethyl)-2-(trifluoromethyl)furan-3-carboxylateHCID 673429093-(5-Chloro-2-hydroxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 673480933-[2-(4-Carboxy-5-trifluoromethyl-furan-2-ylmethoxy)-5-chloro-phenoxy]-azetidine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

The title compound was prepared as described in Example 1 Step D using 3-(5-chloro-2-hydroxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester (0.15 g, 0.50 mmol), the title compound of Step A (0.18 g, 0.60 mmol), Cs2CO3 (0.41 g, 1.2 mmol), KI (0.12 g, 0.70 mmol) in DMF, except upon completion of the reaction 1N NaOH and EtOAc were added. The organic layer was washed with 1N NaOH and dried. The crude material was purified by RP HPLC to provide the title compound. 1H NMR (CDCl3): 7.20-6.92 (m, 1H), 6.91-6.80 (m, 2H), 6.77-6.69 (m, 1H), 6.53 (d, J=2.1 Hz, 1H), 4.87 (s, 2H), 4.79-4.69 (m, 1H), 4.27-4.12 (m, 2H), 4.00-3.88 (m, 2H), 1.38 (s, 9H).

後処理

  1. customThe title compound was prepared
  2. additionwere added
  3. washThe organic layer was washed with 1N NaOH
  4. customdried
  5. customThe crude material was purified by RP HPLC

出典と根拠

ORDレコード
ord-1cb6e87a6de846118fb2db001002fd56
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08642583B2

反応ノート

読み込み中…

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