Trifluoromethanesulfonic acid, lithium salt → methyl (2R)-3-[(4-fluoro-3-methyl-2-oxo-2,3-dihydro-6-benzoxazolyl)amino]-2-hydroxypropanoate

HRID 723926

반응식

HRID 723926 반응식
[NH2:1][C:2]1[CH:12]=[C:11]([F:13])[C:5]2[N:6]([CH3:10])[C:7](=[O:9])[O:8][C:4]=2[CH:3]=1.[CH3:14][O:15][C:16]([C@@H:18]1[O:20][CH2:19]1)=[O:17].FC(F)(F)S([O-])(=O)=O.[Li+]>C(#N)C>[F:13][C:11]1[C:5]2[N:6]([CH3:10])[C:7](=[O:9])[O:8][C:4]=2[CH:3]=[C:2]([NH:1][CH2:19][C@@H:18]([OH:20])[C:16]([O:15][CH3:14])=[O:17])[CH:12]=1

참가 물질

5

반응물 3

HCID 3664839Trifluoromethanesulfonic acid, lithium saltHCID 9877347Methyl (2R)-2-oxiranecarboxylateHCID 684860356-amino-4-fluoro-3-methyl-1,3-benzoxazol-2(3H)-one

생성물 1

HCID 86610080methyl (2R)-3-[(4-fluoro-3-methyl-2-oxo-2,3-dihydro-6-benzoxazolyl)amino]-2-hydroxypropanoate수율 99.6%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
90 °C

실험 절차

A mixture of 6-amino-4-fluoro-3-methyl-1,3-benzoxazol-2(3H)-one (Step 7, 0.630 g, 3.46 mmol), methyl (2R)-glycidate (0.353 g, 3.46 mmol) and lithium trifluoromethanesulfonate (0.540 g, 3.46 mmol) in acetonitrile (10 ml) is stirred and heated at 90° C. overnight. The reaction mixture is diluted with ethyl actetate, washed with water and saline, dried (MgSO4), and evaporated under reduced pressure. Final purification by flash column chromatography (50% ethyl acetate/hexane) gives pure product as a white solid (0.98 g, 60%); MS for C12H13FN2O5 m/z 285 (M+H)+.

후처리

  1. additionThe reaction mixture is diluted with ethyl actetate
  2. washwashed with water and saline
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure
  5. customFinal purification by flash column chromatography (50% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-ef6eff76f4ce4ee6b98b1fc50c0c5592
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141588B2

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