Ammonium Chloride → (S)-5-((dibenzylamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one

HRID 245313노트

반응식

HRID 245313 반응식
[C:1]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[C:14]([F:24])[CH:13]=1)([O:3][CH2:4][C:5]1C=CC=CC=1)=[O:2].CC(C)([O-])C.[Li+].ClC[C@@H](O)[CH2:34][N:35]([CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C.CN(C)C=O>[CH2:43]([N:35]([CH2:34][C@@H:4]1[O:3][C:1](=[O:2])[N:11]([C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)=[C:14]([F:24])[CH:13]=2)[CH2:5]1)[CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

참가 물질

8

반응물 4

HCID 25517Ammonium ChlorideHCID 5306150Carbamic acid, N-(3-fluoro-4-(4-morpholinyl)phenyl)-, phenylmethyl esterHCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)HCID 49765557(S)-1-chloro-3-(dibenzylamino)propan-2-ol

생성물 1

HCID 11213668(S)-5-((dibenzylamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one수율 88.3%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
25 °C

실험 절차

N-carbobenzoxy-3-fluoro-4-morpholinylaniline (0.33 g, 1 mmol) was added under nitrogen atmosphere to 5 mL of DMF (N,N-dimethyl formamide), and mixture was cooled to −10˜0° C. A solution of lithium tert-butoxide (2.5 mL, 2.5 mmol) in tetrahydrofuran was added dropwise. The mixture was warmed to room temperature (25° C.) naturally and stirred for 2 hours. (S)-1-chloro-3-(dibenzylamino)propan-2-ol (0.32 g, 1.1 mmol) was then added and the mixture was stirred at room temperature for 20 hours. Saturated ammonium chloride solution and ethyl acetate were added to separate. The organic layer was washed with water and dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to provide 0.42 g of white solid in 88% yield.

후처리

  1. temperaturewas cooled to −10˜0° C
  2. stirringthe mixture was stirred at room temperature for 20 hours
  3. customto separate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-66f0e0c18c8b4dc1b924d7ee7db236c9
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658789B2

반응 노트

불러오는 중…