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Benzene → (4S,5R)-N-Benzoyl-2-(2,4-dimethoxyphenyl)-4-phenyl-5-oxazolidinecarboxylic acid methyl ester

HRID 1072940
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HRID 1072940 반응식
[CH3:1][O:2][C:3](=[O:22])[CH:4]([OH:21])[CH:5]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH:6][C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1C=CC=CC=1.CO[CH:31](OC)[C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][C:33]=1[O:40][CH3:41].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1COCC1>[CH3:1][O:2][C:3]([C@@H:4]1[O:21][CH:31]([C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][C:33]=2[O:40][CH3:41])[N:6]([C:7](=[O:14])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@H:5]1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:22]
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참가 물질

6

반응물 4

HCID 241BenzeneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 10990203Methyl (2r,3s)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoateHCID 142873251-(Dimethoxymethyl)-2,4-dimethoxybenzene

생성물 1

HCID 57168681(4S,5R)-N-Benzoyl-2-(2,4-dimethoxyphenyl)-4-phenyl-5-oxazolidinecarboxylic acid methyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

N-Benzoyl-βphenyl isoserine methyl ester (3A, 0.5 g, 1.67 mM) is dissolved in dry THF (10 mL) and benzene (10 mL) and the solution treated with 2,4-dimethoxy benzaldehyde dimethyl acetal (4, 0.420 g, 1.98 mM) and pyridinium p-toluenesulfonate (12 mg) and the solution warmed to reflux. After 30 minutes the reaction is cooled to RT and allowed to stand overnight. It is then again warmed to slowly distill off ½ of the solvent over 1 hr. TLC shows the reaction to be finished at this point. The reaction is concentrated in vacuo and the residue chromatographed over 50 g silica gel packed in (5-95) methanol-toluene. The column is eluted with methanol-toluene (5-95). Fractions of 12 mL are collected. The product elutes as a mixture. Thus, fractions containing both 5Aa & 5Ab are recombined and evaporated. The residue (0.90 g) is rechromatographed over silica gel (100 g) The column is eluted with ethyl acetate-toluene (500 mL of 15-85 and 500 mL of 20-80). Fractions of 20 mL are collected and analyzed by TLC. The fractions containing each 5Aa & 5Ab are combined and evaporated under vacuum.

후처리

  1. temperaturethe solution warmed to reflux
  2. temperatureIt is then again warmed
  3. distillationto slowly distill off ½ of the solvent over 1 hr
  4. customthe reaction
  5. concentrationThe reaction is concentrated in vacuo
  6. customthe residue chromatographed over 50 g silica gel
  7. washThe column is eluted with methanol-toluene (5-95)
  8. customFractions of 12 mL are collected
  9. additionThus, fractions containing both 5Aa & 5Ab
  10. customevaporated
  11. customThe residue (0.90 g) is rechromatographed over silica gel (100 g) The column
  12. washis eluted with ethyl acetate-toluene (500 mL of 15-85 and 500 mL of 20-80)
  13. customFractions of 20 mL are collected
  14. additionThe fractions containing each 5Aa & 5Ab
  15. customevaporated under vacuum

출처 및 근거

ORD 기록
ord-d6c9d3f8b3ad43a5ad417876847f7b2d
출처 데이터셋
uspto-grants-2005_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06911549B1

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