Anisole → N-Butyloxycarbonyl-3-{3-[2-(2-ethylimidazol-1-yl)acetyl]phenyl}-5-iso-butyl-thiophene-2-sulfonamide

HRID 659700노트

반응식

HRID 659700 반응식
[CH2:1]([C:3]1[N:4]([CH2:8][C:9]([C:11]2[CH:12]=[C:13]([C:17]3[CH:21]=[C:20]([CH2:22][CH:23]([CH3:25])[CH3:24])[S:19][C:18]=3[S:26]([NH:29]C(C)(C)C)(=[O:28])=[O:27])[CH:14]=[CH:15][CH:16]=2)=[O:10])[CH:5]=[CH:6][N:7]=1)[CH3:2].C1(OC)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+].Cl[C:49]([O:51][CH2:52][CH2:53][CH2:54][CH3:55])=[O:50]>C(O)(C(F)(F)F)=O.C(Cl)Cl.O>[CH2:52]([O:51][C:49]([NH:29][S:26]([C:18]1[S:19][C:20]([CH2:22][CH:23]([CH3:25])[CH3:24])=[CH:21][C:17]=1[C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:9](=[O:10])[CH2:8][N:4]2[CH:5]=[CH:6][N:7]=[C:3]2[CH2:1][CH3:2])[CH:12]=1)(=[O:28])=[O:27])=[O:50])[CH2:53][CH2:54][CH3:55]

참가 물질

8

반응물 4

HCID 7519AnisoleHCID 10340Sodium CarbonateHCID 61140Butyl chloroformateHCID 671329483-{3-[2-(2-Ethylimidazol-1-yl)acetyl]phenyl}-5-iso-butyl-N-tert-butylthio-phene-2-sulfonamide

생성물 1

HCID 67133138N-Butyloxycarbonyl-3-{3-[2-(2-ethylimidazol-1-yl)acetyl]phenyl}-5-iso-butyl-thiophene-2-sulfonamide수율 47%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 6422Trifluoroacetic acid용매

실험 절차

To a solution of 3-{3-[2-(2-ethylimidazol-1-yl)acetyl]phenyl}-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide (74.5 mg, 0.153 mmol; see step (b)) in TFA (3 mL) was added anisole (150 μL) and the reaction mixture was stirred for 28 h at ambient temperature. The reaction mixture was concentrated in vacuo and dried in vacuo overnight. To the crude product dissolved in CH2Cl2 (7 mL) was added Na2CO3 (72.9 mg, 0.688 mmol), water (2 mL) and butyl chloroformate (33.0 μL, 0.260 mmol), and the reaction mixture was stirred overnight at ambient temperature. The reaction mixture was diluted with CH2Cl2 (30 mL) and washed with citric acid (10% aq), brine and water, dried (over anhydrous MgSO4), concentrated in vacuo, and the residue purified by flash chromatography using MeOH:CH2Cl2 (8:92) as eluent to give the sub-title compound in 47% yield, over two steps, (38.5 mg, 0.0724 mmol).

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customdried in vacuo overnight
  3. dissolutionTo the crude product dissolved in CH2Cl2 (7 mL)
  4. stirringthe reaction mixture was stirred overnight at ambient temperature
  5. washwashed with citric acid (10% aq), brine and water
  6. dry with materialdried (over anhydrous MgSO4)
  7. concentrationconcentrated in vacuo
  8. customthe residue purified by flash chromatography

출처 및 근거

ORD 기록
ord-d826f5e7961f4a589d52b59ce5f12f34
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08080571B2

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