Methanesulfonyl chloride → HCID 86603641, 화합물

HRID 226329

반응식

HRID 226329 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10]O)=[CH:9][C:4]=2[CH2:3][CH2:2]1.CS(Cl)(=O)=O.Cl.Cl.[C:19]([O:23][C:24]([N:26]([C@@H:40]1[CH2:44][CH2:43][NH:42][CH2:41]1)[C:27]1[N:32]=[CH:31][C:30](/[CH:33]=[CH:34]/[C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:29][CH:28]=1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>CCN(CC)CC.C1COCC1>[C:19]([O:23][C:24]([N:26]([C@@H:40]1[CH2:44][CH2:43][N:42]([CH2:10][C:8]2[CH:7]=[CH:6][C:5]3[O:1][CH2:2][CH2:3][C:4]=3[CH:9]=2)[CH2:41]1)[C:27]1[N:32]=[CH:31][C:30](/[CH:33]=[CH:34]/[C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:29][CH:28]=1)=[O:25])([CH3:20])([CH3:21])[CH3:22]

참가 물질

6

반응물 3

HCID 31297Methanesulfonyl chlorideHCID 2776158(2,3-Dihydro-1-benzofuran-5-yl)methanolHCID 86603639ethyl (2E)-3-(6-{(tert-butoxycarbonyl)[(3R)-3-pyrrolidinyl]amino}-3-pyridyl)acrylate dihydrochloride

생성물 1

HCID 86603641HCID 86603641, 화합물수율 47.2%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매2회

실험 절차

To a mixture of 2,3-dihydro-1-benzofuran-5-ylmethanol (95.1 mg), Et3N (0.120 mL), and THF (3 mL) was added methanesulfonyl chloride (0.053 mL) at 4° C. The reaction mixture was stirred for 3 hours, and added ethyl (2E)-3-(6-{(tert-butoxycarbonyl)[(3R)-3-pyrrolidinyl]amino}-3-pyridyl)acrylate dihydrochloride (250 mg) and Et3N (0.281 mL). After stirring for 2 hours at 60° C., the resulting mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over MgSO4, filtered, and evaporated in vacuo. The residue was purified by column chromatography on silica gel to give ethyl (2E)-3-(6-{(tert-butoxycarbonyl)[(3R)-1-(2,3-dihydro-1-benzofuran-5-ylmethyl)-3-pyrrolidinyl]amino}-3-pyridyl)acrylate (134 mg).

후처리

  1. stirringAfter stirring for 2 hours at 60° C.
  2. customthe resulting mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-921a89893f8a4239a874a3f306929314
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557127B2

연결된 노트

불러오는 중…