Sodium Azide → (5R)-5-(Azidomethyl)-3-(3-fluorophenyl)-2-oxazolidinone

HRID 583566

반응식

HRID 583566 반응식
CC1C=CC(S(O[CH2:12][C@@H:13]2[O:17][C:16](=[O:18])[N:15]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=3)[CH2:14]2)(=O)=O)=CC=1.[N-:26]=[N+:27]=[N-:28].[Na+]>CN(C=O)C.C(OCC)(=O)C.O>[F:25][C:21]1[CH:20]=[C:19]([N:15]2[CH2:14][C@H:13]([CH2:12][N:26]=[N+:27]=[N-:28])[O:17][C:16]2=[O:18])[CH:24]=[CH:23][CH:22]=1

참가 물질

6

반응물 2

HCID 33557Sodium AzideHCID 54408340(R)-[3-(3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl 4-methylbenzenesulfonate

생성물 1

HCID 11550435(5R)-5-(Azidomethyl)-3-(3-fluorophenyl)-2-oxazolidinone

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of (R)-[3-(3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl 4-methylbenzenesulfonate (PREPARATION 15, 2.340 g, 6.40 mmol) in dry DMF (60 ml) is treated with solid sodium azide (3.331 g, 51.23 mmmol) at 20-25°. The resultant slurry is warmed to 65° for 4.5 hr and then cooled to 20-25° and left overnight. The reaction mixture is then diluted with ethyl acetate and water, transferred to a separatory funnel, and extracted with ethyl acetate. The combined ethyl acetate extracts are washed thoroughly with water, and then dried (sodium sulfate), filtered and concentrated under reduced pressure to give the title compound, mp 81-82°; [α]25D -136.5° (c 0.9, CHCl3); IR (mineral oil mull): 2115, 1736, 1614, 1591, 1586, 1497, 1422, 1233, 1199, 1081, 1049 cm-1 ; NMR (CDCl3, 300 MHz) δ 7.45, 7.34, 7.23, 6.86, 4.81, 4.09, 3.86, 3.72 and 3.60; MS (m/z) 236 (59.0, M+), 179, 136, 122, 109, 95, 75; HRMS (m/z) 236.0708 (calc'd for C10H9FN4O2 : 236.0709).

후처리

  1. temperatureThe resultant slurry is warmed to 65° for 4.5 hr
  2. temperaturecooled to 20-25°
  3. customtransferred to a separatory funnel
  4. extractionextracted with ethyl acetate
  5. washThe combined ethyl acetate extracts are washed thoroughly with water
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-649d99a9f1ee4265b0761a9edfcd6e90
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05929248

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