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

HRID 53352

반응식

HRID 53352 반응식
[C:1]([N:11]1[C@@H:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:14][O:13][C:12]1=[O:22])(=[O:10])/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:23]([N:30]([CH2:34][Si](C)(C)C)[CH2:31]OC)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:23]([N:30]1[CH2:34][C@@H:3]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[C@H:2]([C:1]([N:11]2[C@@H:15]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:14][O:13][C:12]2=[O:22])=[O:10])[CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

참가 물질

6

반응물 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 679769(4S)-4-Phenyl-3-(3-phenylprop-2-enoyl)-1,3-oxazolidin-2-one

생성물 1

HCID 677115143-(trans-1-benzyl-4-phenyl-3-pyrrolidinylcarbonyl)-4-(S)-phenyl-2-oxazolidinone

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

The compound from step 8b (294 mg, 1.2 mmol) was dissolved in toluene (10 mL), and the solution flushed with N2. N-benzyl-N(methoxymethyl)trimethylsilylmethylamine (284 mg, 0.227 mmol) was added, the mixture was stirred for 20 minutes and trifluoroacetic acid (1M, 0.1 mL, 0.10 mmol) was added dropwise. The mixture was stirred for 1.5 hour at room temperature, then diluted with 50 mL of ethyl acetate, washed with 5% aqueous NaHCO3 and dried over Na2SO4. The solvent was removed and the residue was dried under vacuum (542 mg). The isomers were separated by chromatography on silica gel, and the major isomer (3R,4R) was taken to the next step. MS m/z 427 (M+H)+.

후처리

  1. customthe solution flushed with N2
  2. stirringThe mixture was stirred for 1.5 hour at room temperature
  3. washwashed with 5% aqueous NaHCO3
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed
  6. customthe residue was dried under vacuum (542 mg)
  7. customThe isomers were separated by chromatography on silica gel

출처 및 근거

ORD 기록
ord-8ae69679a31b46ce87909e78682d162a
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05618949

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