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

HRID 324599노트

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HRID 324599 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5f308fcb1fbd4fb9bebcb139bbfe14d8
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06218415B1

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