1,1'-Carbonyldiimidazole → methyl(5R)-3-(4-fluoro-3-methyl-2-oxo-2,3-dihydro-6-benzoxazolyl)-2-oxo-5-oxazolidinecarboxylate

HRID 723927

반응식

HRID 723927 반응식
[F:1][C:2]1[C:7]2[N:8]([CH3:12])[C:9](=[O:11])[O:10][C:6]=2[CH:5]=[C:4]([NH:13][CH2:14][C@@H:15]([OH:20])[C:16]([O:18][CH3:19])=[O:17])[CH:3]=1.[C:21](N1C=CN=C1)(N1C=CN=C1)=[O:22]>C(#N)C.C(OCC)(=O)C>[F:1][C:2]1[C:7]2[N:8]([CH3:12])[C:9](=[O:11])[O:10][C:6]=2[CH:5]=[C:4]([N:13]2[CH2:14][C@H:15]([C:16]([O:18][CH3:19])=[O:17])[O:20][C:21]2=[O:22])[CH:3]=1

참가 물질

5

반응물 2

HCID 682631,1'-CarbonyldiimidazoleHCID 86610080methyl (2R)-3-[(4-fluoro-3-methyl-2-oxo-2,3-dihydro-6-benzoxazolyl)amino]-2-hydroxypropanoate

생성물 1

HCID 68489786methyl(5R)-3-(4-fluoro-3-methyl-2-oxo-2,3-dihydro-6-benzoxazolyl)-2-oxo-5-oxazolidinecarboxylate수율 96%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

A mixture of methyl (2R)-3-[(4-fluoro-3-methyl-2-oxo-2,3-dihydro-6-benzoxazolyl)amino]-2-hydroxypropanoate (Step 8, 0.84 g, 2.96 mmol) and 1,1′-carbonyldiimidazole (0.48 g, 2.96 mmol) in acetonitrile is stirred and heated at 60° C. overnight. The reaction is diluted with ethyl acetate, washed with 2N HCl and saline, and evaporated under reduced pressure. The resulting solid is triturated with methanol to give pure product as a white solid (0.88 g, 96%); MS for C13H11FN2O6 m/z 311 (M+H)+.

후처리

  1. washwashed with 2N HCl and saline
  2. customevaporated under reduced pressure
  3. customThe resulting solid is triturated with methanol

출처 및 근거

ORD 기록
ord-214a83b1fd5d426dbba9743b3b7f13a0
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141588B2

연결된 노트

불러오는 중…