Acetic Acid → HCID 72427427, 화합물

HRID 346937노트

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HRID 346937 반응식
[C:1]([O:5][C:6](=[O:52])[NH:7][CH:8]1[C:26](=[O:27])[N:25]2[CH:21]([CH2:22][CH:23]([O:28][C:29]3[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH:32]=[CH:31][N:30]=3)[CH2:24]2)[C:20](=[O:39])[NH:19][C:18]2([C:40]([NH:42][S:43]([C:46]3([CH2:49][CH2:50][CH3:51])[CH2:48][CH2:47]3)(=[O:45])=[O:44])=[O:41])[CH:16]([CH2:17]2)[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].N(C([O-])=O)=NC([O-])=O.[K+].[K+].C(O)(=O)C>CO>[C:1]([O:5][C:6](=[O:52])[NH:7][CH:8]1[C:26](=[O:27])[N:25]2[CH:21]([CH2:22][CH:23]([O:28][C:29]3[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH:32]=[CH:31][N:30]=3)[CH2:24]2)[C:20](=[O:39])[NH:19][C:18]2([C:40]([NH:42][S:43]([C:46]3([CH2:49][CH2:50][CH3:51])[CH2:47][CH2:48]3)(=[O:44])=[O:45])=[O:41])[CH:16]([CH2:17]2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 176Acetic Acid2회HCID 6096233Potassium diazene-1,2-dicarboxylate2회HCID 68751392[18-(Isoquinolin-1-yloxy)-2,15-dioxo-4-(1-propyl-cyclopropanesulfonylaminocarbonyl)-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-7-en-14-yl]-carbamic acid tert-butyl ester

생성물 1

HCID 72427427HCID 72427427, 화합물수율 34%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

To a mixture of 73 mg (0.1 mmol) of [18-(Isoquinolin-1-yloxy)-2,15-dioxo-4-(1-propylcyclopropanesulfonylamino-carbonyl)-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-7-en-14-yl]-carbamic acid tert-butyl ester in 3 mL of methanol was added 332 mg (2 mmol)of dipotassium azodicarboxylate. Glacial acetic acid (240 mg, 4 mmol) in 2 mL of methanol was added slowly by a syringe pump over 5 h. The mixture was stirred at rt. After 5 h, another 332 mg (2 mmol) of dipotassium azodicarboxylate and 240 mg (4 mmol) of glacial acetic acid was added over the course of 5 h and the stirring was continued overnight. This cycle was repeated twice. LC-MS showed about 40% starting material still remaining. The solvent was then removed on a rotary evaporator. Water was added to the residue and the mixture was extracted three times with ethyl acetate. It was then dried with magnesium sulfate, filtered and concentrated in vacuo. The resulting oil was dissolved in methanol and purified by preparative HPLC (YMC ODS-A, S5, 20×100 mm, gradient: 80% B to 85% B, 15 min, hold 2 min, flow rate 25 mL/min) to isolate the product as a white powder (25 mg, 34%).

후처리

  1. waitthe stirring was continued overnight
  2. customThe solvent was then removed on a rotary evaporator
  3. additionWater was added to the residue
  4. extractionthe mixture was extracted three times with ethyl acetate
  5. dry with materialIt was then dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. dissolutionThe resulting oil was dissolved in methanol
  9. custompurified by preparative HPLC (YMC ODS-A, S5, 20×100 mm, gradient: 80% B to 85% B, 15 min, hold 2 min, flow rate 25 mL/min)

출처 및 근거

ORD 기록
ord-403ed41133ee497b9d2109c086706b9b
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173004B2

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