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

HRID 53352

反応式

HRID 53352 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-8ae69679a31b46ce87909e78682d162a
出典データセット
uspto-grants-1997_04
特許番号
US05618949

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