Acetic Acid → 6-(Benzenesulphonylmethyl)-2-(cyanomethylamino)-3-(furan-3-yl)benzoic acid

HRID 2177685ノート

反応式

HRID 2177685 の反応式
[C:1]1([S:7]([CH2:10][C:11]2[C:20]3[C:19](=[O:21])[O:18][CH2:17][NH:16][C:15]=3[C:14]([C:22]3[CH:26]=[CH:25][O:24][CH:23]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C-:27]#[N:28].[Na+].C(O)(=O)C>CS(C)=O.O>[C:1]1([S:7]([CH2:10][C:11]2[C:20]([C:19]([OH:18])=[O:21])=[C:15]([NH:16][CH2:17][C:27]#[N:28])[C:14]([C:22]3[CH:26]=[CH:25][O:24][CH:23]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

6

反応物 3

HCID 176Acetic AcidHCID 8929Sodium CyanideHCID 671078635-(Benzenesulphonylmethyl)-8-(furan-3-yl)-1,2-dihydro-benzo[d][1,3]oxazin-4-one2 回

生成物 1

HCID 866771096-(Benzenesulphonylmethyl)-2-(cyanomethylamino)-3-(furan-3-yl)benzoic acid収率 85.9%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

A solution of 5-(benzenesulphonylmethyl)-8-(furan-3-yl)-1,2-dihydro-benzo[d][1,3]oxazin-4-one (Intermediate 210, 0.115 g) and sodium cyanide (0.03 g) in DMSO (4 ml) was stirred and heated at 60° C. for 2 hours. After cooling, the mixture was diluted with water, acidified with acetic acid and extracted with ethyl acetate. The organic layer was dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of DCM:methanol:water:acetic acid (350:20:3:2). The product was crystallized from DCM and cyclohexane to give 6-(benzenesulphonylmethyl)-2-(cyanomethylamino)-3-(furan-3-yl)benzoic acid (0.106 g).

後処理

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was purified by chromatography on silica
  7. washeluting with a mixture of DCM:methanol:water:acetic acid (350:20:3:2)
  8. customThe product was crystallized from DCM and cyclohexane

出典と根拠

ORDレコード
ord-e8116ae4bb644782b62c91389c819b25
出典データセット
uspto-grants-2015_06
特許番号
US09067905B2

反応ノート

読み込み中…