Tetrahydrofuran → HCID 86731028, 화합물

HRID 2280212노트

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HRID 2280212 반응식
[C:1]([C:3]1[C:7]2[CH2:8][C@@H:9]3[C@@H:14]([CH2:15][C:6]=2[S:5][C:4]=1[N:23]([CH3:31])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[N:13]([CH3:16])[CH2:12][C@H:11]([C:17](=[O:22])[NH:18][CH2:19][CH2:20][CH3:21])[CH2:10]3)#[N:2].O1CCCC1.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].O1CCCC1.Cl[C:53]([O:55][C:56]1[CH:61]=[CH:60][C:59]([N+:62]([O-:64])=[O:63])=[CH:58][CH:57]=1)=[O:54]>C(OCC)(=O)C.O>[C:26]([O:25][C:24]([N:23]([CH3:31])[C:4]1[S:5][C:6]2[CH2:15][C@@H:14]3[C@H:9]([CH2:10][C@@H:11]([C:17]([N:18]([CH2:19][CH2:20][CH3:21])[C:53](=[O:54])[O:55][C:56]4[CH:57]=[CH:58][C:59]([N+:62]([O-:64])=[O:63])=[CH:60][CH:61]=4)=[O:22])[CH2:12][N:13]3[CH3:16])[CH2:8][C:7]=2[C:3]=1[C:1]#[N:2])=[O:30])([CH3:29])([CH3:28])[CH3:27]

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 821294-Nitrophenyl chloroformateHCID 23700795NaHMDS tetrahydrofuranHCID 86731026HCID 86731026, 화합물

생성물 1

HCID 86731028HCID 86731028, 화합물수율 71.8%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of tert-butyl N-[(4aR*,6R*,8aR*)-3-cyano-8-methyl-6-(propylcarbamoyl)-4H,4aH,5H,6H,7H,8H,8aH,9H-thieno[3,2-g]quinolin-2-yl]-N-methylcarbamate (412 mg) and tetrahydrofuran (5 mL) was added a 1 mol/L sodium hexamethyldisilazide-tetrahydrofuran solution (1.2 mL) at −40° C. After stirring at the same temperature for 20 minutes, 4-nitrophenyl chloroformate (242 mg) was added to the mixture, and then stirred for 1 hour. After warming to room temperature and stirring for 1.5 hours, water and ethyl acetate were added. After the separated organic layer was dried over anhydrous sodium sulfate, it was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 80%-100% ethyl acetate/hexane, gradient elution) to give 4-nitrophenyl N-{[(4aR*,6R*,8aR*)-2-{[(tert-butoxy)carbonyl](methyl)amino}-3-cyano-8-methyl-4H,4aH,5H,6H,7H,8H,8aH,9H-thieno[3,2-g]quinolin-6-yl]carbonyl}-N-propylcarbamate (405 mg).

후처리

  1. stirringstirred for 1 hour
  2. stirringstirring for 1.5 hours
  3. dry with materialAfter the separated organic layer was dried over anhydrous sodium sulfate, it
  4. concentrationwas concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: 80%-100% ethyl acetate/hexane, gradient elution)

출처 및 근거

ORD 기록
ord-433f9602b3144fd3b9b26f4e8bbf0a24
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09138434B2

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