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

HRID 583566

反応式

HRID 583566 の反応式
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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-649d99a9f1ee4265b0761a9edfcd6e90
出典データセット
uspto-grants-1999_07
特許番号
US05929248

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