Acetoxyacetyl chloride → 3-[2-((R)-6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]-oxazolidine-2,4-dione

HRID 251871노트

반응식

HRID 251871 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][C@H:5]2[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH2:20].C[Si](C)(C)[N-][Si](C)(C)C.[Na+].[C:31]([O:34][CH2:35][C:36](Cl)=[O:37])(=[O:33])C>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][C@H:5]2[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[C:36](=[O:37])[CH2:35][O:34][C:31]1=[O:33]

참가 물질

5

반응물 3

HCID 26297Acetoxyacetyl chlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 66864574(R)-2-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylamine

생성물 1

HCID 117180843-[2-((R)-6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]-oxazolidine-2,4-dione

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

(R)-2-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylamine (300 mg, enantiomer B, preparation as described in WO2004085404) was dissolved in absolute THF (10 ml) and admixed at room temperature with stirring with sodium hexamethyl-disilazide solution (0.5 ml; 2 M in THF). After 30 min, acetoxyacetyl chloride (77 μl) was added and the mixture was stirred at room temperature for 2 h. Subsequently, the reaction mixture was concentrated, the residue was dissolved in ethyl acetate/water and basified with sodium hydrogencarbonate solution, and the phases were separated. The aqueous phase was extracted three times with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated. 380 mg of the desired product were obtained. 40 mg thereof were dissolved in acetonitrile/water, acidified with 0.1 N hydrochloric acid and freeze-dried.

후처리

  1. customadmixed at room temperature
  2. concentrationSubsequently, the reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate/water
  4. customthe phases were separated
  5. extractionThe aqueous phase was extracted three times with ethyl acetate
  6. dry with materialThe combined extracts were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-59808eeaed50428bb904d24a5874807b
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868003B2

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