(Methoxycarbonylsulfamoyl)triethylammonium hydroxide → 5-[2-Pyridin-4-yl-5-(1,2,3,6-tetrahydro-pyridin-4-yl)-furan-3-yl]-indan-1-one oxime

HRID 271521

반응식

HRID 271521 반응식
O[C:2]1([C:8]2[O:12][C:11]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[C:10]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[C:24](=[N:28][OH:29])[CH2:23][CH2:22]4)[CH:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[OH-].COC(NS([N+](CC)(CC)CC)(=O)=O)=O>C1COCC1.C(OCC)(=O)C.O>[N:16]1[CH:17]=[CH:18][C:13]([C:11]2[O:12][C:8]([C:2]3[CH2:7][CH2:6][NH:5][CH2:4][CH:3]=3)=[CH:9][C:10]=2[C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[C:24](=[N:28][OH:29])[CH2:23][CH2:22]3)=[CH:14][CH:15]=1

참가 물질

6

반응물 2

HCID 11032497(Methoxycarbonylsulfamoyl)triethylammonium hydroxideHCID 1363552515-[5-(4-Hydroxy-piperidin-4-yl)-2-pyridin-4-yl-furan-3-yl]-indan-1-one oxime

생성물 1

HCID 1363552525-[2-Pyridin-4-yl-5-(1,2,3,6-tetrahydro-pyridin-4-yl)-furan-3-yl]-indan-1-one oxime수율 60.6%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of the product of Example 29, Step 1 (1.06 g, 2.0 mmol) in THF (25 ml) at 0° C. was treated with (methoxycarbonylsulfamoyl)-triethylammonium hydroxide inner salt (Burgess reagent, 952 mg, 4 mmol). After 18 hours at room temperature the mixture was diluted with ethyl acetate and water. The organic phase was washed with water and brine, dried and concentrated in vacuo. Purification of the residue by silica gel chromatography gave the title compound (450 mg, 46%); MS(ES+) m/e 486 [M+H]+.

후처리

  1. washThe organic phase was washed with water and brine
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customPurification of the residue by silica gel chromatography

출처 및 근거

ORD 기록
ord-1949900c95ff40e99c4c6963f76343fb
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452906B2

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