Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → (4S,5R)-N-Carbobenzyloxy-2-(2,4-dimethoxyphenyl)-4-phenyl-5-oxazolidinecarboxylic acid methyl ester

HRID 1072943ノート

反応式

HRID 1072943 の反応式
[CH3:1][O:2][C:3](=[O:24])[CH:4]([OH:23])[CH:5]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[NH:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].COC(=O)[C@H](O)[C@H](C1C=CC=CC=1)NC(OCC1C=CC=CC=1)=O.CO[CH:51](OC)[C:52]1[CH:57]=[CH:56][C:55]([O:58][CH3:59])=[CH:54][C:53]=1[O:60][CH3:61].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:23][CH:51]([C:52]2[CH:57]=[CH:56][C:55]([O:58][CH3:59])=[CH:54][C:53]=2[O:60][CH3:61])[N:6]([C:7]([O:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:8])[C@H:5]1[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:24]

参加物

6

反応物 4

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 142873251-(Dimethoxymethyl)-2,4-dimethoxybenzeneHCID 22389496N-Carbobenzyloxy-beta-phenyl isoserine methyl esterHCID 22865499(2R,3S)-N-carbobenzyloxy-beta-phenyl isoserine methyl ester

生成物 1

HCID 57035355(4S,5R)-N-Carbobenzyloxy-2-(2,4-dimethoxyphenyl)-4-phenyl-5-oxazolidinecarboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

N-Carbobenzyloxy-β-phenyl isoserine methyl ester (Preparation No. 19, 3C, 0.375 g, 1.14 mM) is dissolved in dry THF (10 mL) and the solution treated with 2,4-dimethoxy benzaldehyde dimethyl acetal (4, 0.300 g, 1.42 mM) and pyridinium p-toluenesulfonate (10 mg) and the solution heated to distill off the THF and methanol. After ½ the THF is distilled off, THF (10 mL) is added and the reaction distilled to ½ volume again. The process is repeated three times. The reaction is then concentrated in vacuo and the residue chromatographed over 75 g silica gel packed and eluted in acetone-hexane (300 mL of 20-80 and 300 mL of 25-75). Fractions of 20 mL are collected and analyzed by TLC. The following fractions are combined and evaporated under vacuum.

後処理

  1. temperaturethe solution heated
  2. distillationto distill off the THF and methanol
  3. distillationis distilled off
  4. additionTHF (10 mL) is added
  5. distillationthe reaction distilled
  6. concentrationThe reaction is then concentrated in vacuo
  7. customthe residue chromatographed over 75 g silica gel
  8. washeluted in acetone-hexane (300 mL of 20-80 and 300 mL of 25-75)
  9. customFractions of 20 mL are collected
  10. customevaporated under vacuum

出典と根拠

ORDレコード
ord-f7b7d1a0e4cd4bbc9fab5868e6e61bbe
出典データセット
uspto-grants-2005_06
特許番号
US06911549B1

反応ノート

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