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

HRID 2177685노트

반응식

HRID 2177685 반응식
[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

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 8929Sodium CyanideHCID 671078635-(Benzenesulphonylmethyl)-8-(furan-3-yl)-1,2-dihydro-benzo[d][1,3]oxazin-4-one2회

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e8116ae4bb644782b62c91389c819b25
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09067905B2

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