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Sodium Azide → tert-Butyl 4(S)-(2(S)-azidomethyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 507832
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HRID 507832 반응식
CS(O[CH2:6][C@H:7]([CH:23]([CH3:25])[CH3:24])[CH2:8][C@H:9]1[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[N:10]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])(=O)=O.[N-:26]=[N+:27]=[N-:28].[Na+]>CN1CCCN(C)C1=O>[N:26]([CH2:6][C@H:7]([CH:23]([CH3:25])[CH3:24])[CH2:8][C@H:9]1[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[N:10]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[N+:27]=[N-:28]
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4

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HCID 33557Sodium AzideHCID 86613455tert-Butyl 4(S)-(2(S)-methanesulphonyloxymethyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate

생성물 1

HCID 86613454tert-Butyl 4(S)-(2(S)-azidomethyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate

시약·촉매·용매 1

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-용매

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온도
50 °C

실험 절차

The mixture of 3.47 g of tert-butyl 4(S)-(2(S)-methanesulphonyloxymethyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxyiate and 3.57 g of sodium azide in 50 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone is stirred at 50° C. over 3 hours. The reaction mixture is cooled, poured onto water and extracted with diethyl ether (3×). The combined organic phases are washed successively with water (2×) and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) as a slightly yellowish oil. Rf=0.63 (1:1 EtOAc-heptane); Rt=5.86 (gradient I).

후처리

  1. temperatureThe reaction mixture is cooled
  2. additionpoured onto water
  3. extractionextracted with diethyl ether (3×)
  4. washThe combined organic phases are washed successively with water (2×) and brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated by evaporation

출처 및 근거

ORD 기록
ord-1dd25da4b46f4613ae0bd8ebbeb3c7d5
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07786307B2

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