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Trifluoroacetic acid → 3-(trans-1-benzyl-4-ethyl-3-pyrrolidinylcarbonyl)-4-(S)-phenyl-2-oxazolidinone

HRID 53349
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HRID 53349 반응식
[C:1]([N:7]1[C@@H:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][O:9][C:8]1=[O:18])(=[O:6])/[CH:2]=[CH:3]/[CH2:4][CH3:5].[CH2:19]([N:26]([CH2:30][Si](C)(C)C)[CH2:27]OC)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:19]([N:26]1[CH2:30][C@@H:3]([CH2:4][CH3:5])[C@H:2]([C:1]([N:7]2[C@@H:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:10][O:9][C:8]2=[O:18])=[O:6])[CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
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참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 11096863(S,E)-3-(pent-2-enoyl)-4-phenyloxazolidin-2-one

생성물 1

HCID 228718283-(trans-1-benzyl-4-ethyl-3-pyrrolidinylcarbonyl)-4-(S)-phenyl-2-oxazolidinone

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

The compound from step 7b (490 mg, 2 mmol) was dissolved in methylene chloride (9 mL), and the solution was cooled to 0° C. and flushed with N2. N-benzyl-N-(methoxymethyl)trimethylsilylmethylamine (498 mg, 2.1 mmol) was added, the mixture was stirred for 20 minutes and trifluoroacetic acid (1M, 0.2 mL, 0.20 mmol) was added dropwise over 20 minutes with stirring at 0° C. The mixture was stirred at 0° C. for 1 hour and at room temperature for 24 hours, then diluted with 50 mL of methylene chloride, washed with 10% aqueous K2CO3 and dried over Na2SO4. The solvent was removed and the residue was dried under vacuum (767 mg). The isomers were separated by medium pressure liquid chromatography on silica gel, eluting with 0.5% methanol/methylene chloride. The major isomer (3R,4R) (290 mg) was taken to the next step. MS m/z 379 (M+H)+.

후처리

  1. customflushed with N2
  2. stirringwith stirring at 0° C
  3. stirringThe mixture was stirred at 0° C. for 1 hour and at room temperature for 24 hours
  4. washwashed with 10% aqueous K2CO3
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed
  7. customthe residue was dried under vacuum (767 mg)
  8. customThe isomers were separated by medium pressure liquid chromatography on silica gel
  9. washeluting with 0.5% methanol/methylene chloride

출처 및 근거

ORD 기록
ord-e9e7af725d444411bc88110b648a0b08
출처 데이터셋
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05618949

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