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2,4,6-Triisopropylbenzenesulfonyl azide → 3-azido-1-(2,2,2-trifluoroethyl)-4-(2,4,6-trimethoxybenzyl)-3,4-dihydro-1H-1,4-benzodiazepine-2,5dione

HRID 2213340
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HRID 2213340 반응식
[F:1][C:2]([F:31])([F:30])[CH2:3][N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8](=[O:15])[N:7]([CH2:16][C:17]2[C:22]([O:23][CH3:24])=[CH:21][C:20]([O:25][CH3:26])=[CH:19][C:18]=2[O:27][CH3:28])[CH2:6][C:5]1=[O:29].CC(C)([O-])C.[K+].C(C1C=C(C(C)C)C=C(C(C)C)C=1S([N:56]=[N+:57]=[N-:58])(=O)=O)(C)C.C(=O)([O-])O.[Na+]>C1COCC1.C(O)(=O)C>[N:56]([CH:6]1[N:7]([CH2:16][C:17]2[C:18]([O:27][CH3:28])=[CH:19][C:20]([O:25][CH3:26])=[CH:21][C:22]=2[O:23][CH3:24])[C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:4]([CH2:3][C:2]([F:1])([F:30])[F:31])[C:5]1=[O:29])=[N+:57]=[N-:58]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 3717072,4,6-Triisopropylbenzenesulfonyl azideHCID 516892Sodium BicarbonateHCID 219556511-(2,2,2-trifluoroethyl)4-(2,4,6-trimethoxybenzyl)-3,4-dihydro-1H-1,4benzodiazepine-2,5-dioneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 219558003-azido-1-(2,2,2-trifluoroethyl)-4-(2,4,6-trimethoxybenzyl)-3,4-dihydro-1H-1,4-benzodiazepine-2,5dione

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8028Tetrahydrofuran용매3회

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온도
-78 °C

실험 절차

The product from Step 4C (1 g, 0.0023 mol) was dissolved in THF (30 ml) under nitrogen, cooled to −78° C. and potassium tert butoxide (0.28 g, 0.0025 mol) as a solution in THF (5 ml) added over 10 minutes. 2,4,6-Triisopropylbenzenesulfonyl azide (1.65 g, 0.005 mol) in THF (5 ml) was added dropwise and the mixture stirred for 10 minutes. Glacial acetic acid (0.6 ml) was added and the reaction mixture allowed to attain room temperature and left to stir for 4 hours. The reaction mixture was poured into sodium hydrogen carbonate solution and extracted (ethyl acetate ×2). The combined organic layers were washed (brine), dried (MgSO4) and evaporated in vacuo to give the desired azide which was used without further purification.

후처리

  1. customto attain room temperature
  2. waitleft
  3. stirringto stir for 4 hours
  4. extractionextracted (ethyl acetate ×2)
  5. washThe combined organic layers were washed (brine)
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-57f35610585c41b38f0270a7fb4540bd
출처 데이터셋
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07105509B2

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