Formic Acid → {4-[(E)-3-(3-Chloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-acetaldehyde

HRID 1867357ノート

反応式

HRID 1867357 の反応式
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]([N:12]2[CH2:18][CH2:17][C:16](=[O:19])[N:15]([CH2:20][CH:21](OCC)[O:22]CC)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][CH:7]=1.C(O)=O.O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]([N:12]2[CH2:18][CH2:17][C:16](=[O:19])[N:15]([CH2:20][CH:21]=[O:22])[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 284Formic AcidHCID 962WaterHCID 684321531-[(E)-3-(3-Chloro-phenyl)-acryloyl]-4-(2,2-diethoxy-ethyl)-[1,4]diazepan-5-one

生成物 1

HCID 86615865{4-[(E)-3-(3-Chloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-acetaldehyde収率 45.6%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of 1.00 g (2.53 mmol) of 1-[(E)-3-(3-chloro-phenyl)-acryloyl]-4-(2,2-diethoxy-ethyl)-[1,4]diazepan-5-one in 10 ml of toluene was treated at RT with 5.22 ml formic acid and 1.5 ml water. The reaction was stirred for 1.5 h, evaporated and neutralized with aqueous saturated NaHCO3 and extracted with Et2O (3×). The organic phases were washed with aqueous 10% NaCl, dried over Na2SO4 evaporated and purified by flash silica gel column (EtOAc) to yield 0.37 g (45%) of the title compound as off-white foam. MS: 321.3 (MH+, Cl).

後処理

  1. customevaporated
  2. extractionextracted with Et2O (3×)
  3. washThe organic phases were washed with aqueous 10% NaCl
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. custompurified by flash silica gel column (EtOAc)

出典と根拠

ORDレコード
ord-4c256c09299f4815929677b541b84b1c
出典データセット
uspto-grants-2009_12
特許番号
US07632829B2

反応ノート

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