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Water → Ethyl 2-(2-thioxo-2,3-dihydrobenzoxazol-5-yl)propionate

HRID 660317
ノート
印刷プレビュー

反応式

HRID 660317 の反応式
[CH2:1]([O:3][C:4](=[O:15])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([NH2:14])[CH:8]=1)[CH3:6])[CH3:2].C1C=CC(O[C:23](Cl)=[S:24])=CC=1.C1CCN2C(=NCCC2)CC1.O>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:15])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]2[O:13][C:23](=[S:24])[NH:14][C:9]=2[CH:8]=1)[CH3:6])[CH3:2]
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 4

HCID 962WaterHCID 70498Phenyl thioxochloroformateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 12202638Ethyl 3-amino-4-hydroxy-phenyl-propionate

生成物 1

HCID 20319623Ethyl 2-(2-thioxo-2,3-dihydrobenzoxazol-5-yl)propionate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide
溶媒

実験手順

A solution of 2-(3-amino-4-hydroxy-phenyl)-propionic acid ethyl ester (370 mg) in DMF (2 mL) was added phenyl chlorothionoformate (380 mg in DMF), and DBU (540 mg, in DMF) at room temperature. The reaction mixture was stirred for 16 h at room temperature and water was added to this mixture. The resulting mixture was extracted with ethyl ether. The combined organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting residue was chromatographed on silica gel (n-Hex:EtOAc=4:1) to afford the product as white solid. (130 mg, 29.2%)

後処理

  1. extractionThe resulting mixture was extracted with ethyl ether
  2. dry with materialThe combined organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was chromatographed on silica gel (n-Hex:EtOAc=4:1)

出典と根拠

ORDレコード
ord-d47d54ef4c0341d2af21bb3d8816303e
出典データセット
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08084484B2

反応ノート

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