Triethylamine → [(S)-2-((S)-8-Azidomethyl-7,8-dihydro-[1,4]dioxino[2,3-g]indazol-1-yl)-1-methyl-ethyl]-carbamic acid benzyl ester

HRID 31369

반응식

HRID 31369 반응식
[CH2:1]([O:8][C:9](=[O:29])[NH:10][C@@H:11]([CH3:28])[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]3[O:25][CH2:24][C@H:23]([CH2:26]O)[O:22][C:20]3=2)[CH:15]=[N:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.CS(OS(C)(=O)=O)(=O)=O.[N-:46]=[N+:47]=[N-:48].[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1.CS(C)=O>[CH2:1]([O:8][C:9](=[O:29])[NH:10][C@@H:11]([CH3:28])[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]3[O:25][CH2:24][C@H:23]([CH2:26][N:46]=[N+:47]=[N-:48])[O:22][C:20]3=2)[CH:15]=[N:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 33557Sodium AzideHCID 81560Methanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 69253876[(S)-2-((S)-8-Hydroxymethyl-7,8-dihydro-[1,4]dioxino[2,3-g]indazol-1-yl)-1-methyl-ethyl]-carbamic acid benzyl ester

생성물 1

HCID 86605342[(S)-2-((S)-8-Azidomethyl-7,8-dihydro-[1,4]dioxino[2,3-g]indazol-1-yl)-1-methyl-ethyl]-carbamic acid benzyl ester수율 63.6%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8028Tetrahydrofuran용매

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온도
95 °C

실험 절차

To a ° C. stirred solution of the alcohol from Step B of Example 1 (0.43 g, 1.08 mmol) in anhydrous tetrahydrofuran (30 mL) was added triethylamine (0.88 g, 8.6 mmol) and methanesulfonic anhydride (0.76 g, 4.4 mmol) under nitrogen atmosphere. After 1 h the volatiles were evaporated. To the residue was added anhydrous DMSO (30 mL) and sodium azide (0.7 g, 11 mmol). The resulting mixture was heated at 85° C. for 3 h, 95° C. for 1 h, cooled, mixed with a saturated aqueous solution of sodium bicarbonate (100 mL) and extracted with ethyl acetate (50 mL×3). Chromatography on silica eluting with a gradient of 15% to 60% ethyl acetate/hexane gave an oil (0.29 g, 63%): LCMS (+APCI) 423 (M+H).

후처리

  1. customAfter 1 h the volatiles were evaporated
  2. temperaturecooled
  3. extractionextracted with ethyl acetate (50 mL×3)

출처 및 근거

ORD 기록
ord-d1cceb88858441c9958bd9027dd19f57
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425572B2

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