Trifluoroacetic acid → (R)-3-((S)-1-benzyl-3-methylpyrrolidine-3-carbonyl)-4-phenyloxazolidin-2-one

HRID 338825

반응식

HRID 338825 반응식
[C:1]([N:6]1[C@H:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9][O:8][C:7]1=[O:17])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:18](O)(C(F)(F)F)=O.[CH2:25]([N:32](C[Si](C)(C)C)[CH2:33]OC)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1(C)C=CC=CC=1>[CH2:25]([N:32]1[CH2:33][CH2:4][C@:2]([CH3:18])([C:1]([N:6]2[C@H:10]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:9][O:8][C:7]2=[O:17])=[O:5])[CH2:3]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 677330(R)-3-methacryloyl-4-phenyloxazolidin-2-one

생성물 1

HCID 70983198(R)-3-((S)-1-benzyl-3-methylpyrrolidine-3-carbonyl)-4-phenyloxazolidin-2-one수율 683.5%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of (R)-3-methacryloyl-4-phenyloxazolidin-2-one (135.00 g, 583.79 mmol) and TFA (4.497 mL, 58.379 mmol) in dry toluene (50 mL) at <10° C. was quickly added dropwise N-benzyl-1-methoxy-N-((trimethylsilyl)methyl)methanamine (194.16 mL, 758.93 mmol), and the mixture was stirred at ambient temperature overnight. The reaction was filtered and the filtrate was extracted with 4N HCl (3×250 mL). The aqueous layer was washed with ethyl acetate (250 mL) then made basic with solid K2CO3 to pH 10. The basic aqueous layer was extracted with ethyl acetate (4×400 mL), dried (MgSO4), filtered and concentrated under reduced pressure to provide (R)-3-((S)-1-benzyl-3-methylpyrrolidine-3-carbonyl)-4-phenyloxazolidin-2-one (145 g, 399 mmol, 68% yield) as a dark oil.

후처리

  1. filtrationThe reaction was filtered
  2. extractionthe filtrate was extracted with 4N HCl (3×250 mL)
  3. washThe aqueous layer was washed with ethyl acetate (250 mL)
  4. extractionThe basic aqueous layer was extracted with ethyl acetate (4×400 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-02446b8d51614e65beb02f4f717ac37d
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889704B2

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