Tetrahydrofuran → Methyl 2,3-dimethyl-2-[(1-oxo-2,3-benzoxazin-4-yl)amino]butyrate

HRID 249190

반응식

HRID 249190 반응식
[NH2:1][C:2]([CH3:10])([CH:7]([CH3:9])[CH3:8])[C:3]([O:5][CH3:6])=[O:4].C([N:13]([CH2:16][CH3:17])CC)C.O1CCCC1.ClC([C:26]1[CH:41]=[CH:40][CH:39]=C[C:27]=1[C:28]([O:30]CC1C=CC=CC=1)=[O:29])=O>C(Cl)Cl>[CH3:10][C:2]([NH:1][C:16]1[C:17]2[CH:39]=[CH:40][CH:41]=[CH:26][C:27]=2[C:28](=[O:29])[O:30][N:13]=1)([CH:7]([CH3:9])[CH3:8])[C:3]([O:5][CH3:6])=[O:4]

참가 물질

6

반응물 4

HCID 8028Tetrahydrofuran2회HCID 8471TriethylamineHCID 13018902Methyl 2-amino-2,3-dimethylbutanoateHCID 22127333Benzyl o-(chloroformyl)benzoate

생성물 1

HCID 15029344Methyl 2,3-dimethyl-2-[(1-oxo-2,3-benzoxazin-4-yl)amino]butyrate수율 40%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of methyl 2-amino-2,3-dimethylbutyrate (2.76 g, 0.019 mol), and triethylamine (1.97 g, 0.0195 mol) and tetrahydrofuran is added dropwise to a 5° C. mixture of benzyl o-(chloroformyl)benzoate, o-oxime(6.0 g, 0.02 mol) (which is prepared following the procedure in examples 1 and 2) and tetrahydrofuran under a nitrogen stream. The reaction mixture is stirred at room temperature for 21 hours, filtered to remove solids and the filtrate is concentrated in vacuo to give a yellow oil. The oil is dissolved into methylene chloride. The methylene chloride solution is washed sequentially with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give a yellow oil. Crystallization of the oil from a benzene/hexanes/methylene chloride solution yields a white solid. The solid is chromatographed using neutral alumina and 4% ethyl acetate in methylene chloride as eluent to give the title compound as a white solid (2.41 g, 40%), mp 132°-134°, identified by IR and NMR spectral analyses.

후처리

  1. customis prepared
  2. filtrationfiltered
  3. customto remove solids
  4. concentrationthe filtrate is concentrated in vacuo
  5. customto give a yellow oil
  6. washThe methylene chloride solution is washed sequentially with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customto give a yellow oil
  10. customCrystallization of the oil from a benzene/hexanes/methylene chloride solution
  11. customyields a white solid
  12. customThe solid is chromatographed

출처 및 근거

ORD 기록
ord-f52a0b90094248f59a372d878f44c1c3
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05213607

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