Trityl chloride → N-(Triphenylmethyl)-L-serine methyl ester

HRID 324599ノート

反応式

HRID 324599 の反応式
[C:1](Cl)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:22][O:23][C:24](=[O:29])[C@H:25]([CH2:27][OH:28])[NH2:26].C(N(CC)CC)C>C1COCC1>[CH3:22][O:23][C:24](=[O:29])[C@H:25]([CH2:27][OH:28])[NH:26][C:1]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)

生成物 1

HCID 7128367N-(Triphenylmethyl)-L-serine methyl ester収率 58%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A solution of 10.75 g (38.56 mmol) of trityl chloride is added, at 0° C., to a solution of 6 g (38.56 mmol) of L-serine methyl ester hydrochloride and 7.8 g (77.12 mmol) of triethylamine in absolute THF and this solution is left to stir at 0° C. for 4 h and then at room temperature for 2 days. The solvent is removed in vacuo and the residue is partitioned between dichloromethane and a 10% aqueous solution of citric acid. The phases are separated and the organic phase is washed with water and dried over sodium sulfate. Following filtration, the solvent is removed in vacuo and the residue is chromatographed through silica gel using heptane/ethyl acetate=6/4. 8 g (58%) of (34.3) are obtained after concentrating the product fractions.

後処理

  1. waitthis solution is left
  2. waitat room temperature for 2 days
  3. customThe solvent is removed in vacuo
  4. customthe residue is partitioned between dichloromethane
  5. customThe phases are separated
  6. washthe organic phase is washed with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltration
  9. customthe solvent is removed in vacuo
  10. customthe residue is chromatographed through silica gel

出典と根拠

ORDレコード
ord-5f308fcb1fbd4fb9bebcb139bbfe14d8
出典データセット
uspto-grants-2001_04
特許番号
US06218415B1

反応ノート

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