Imidazole → 2-(t-Butoxycarbonylamino)-3-(t-butyldiphenylsiloxy)propanol

HRID 352867

反応式

HRID 352867 の反応式
N1C=CN=C1.CO[C:8](=[O:20])[C@H:9]([CH2:18][OH:19])[NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].[Si:21](Cl)([C:34]([CH3:37])([CH3:36])[CH3:35])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(OCC)(=O)C>CN(C)C=O.O1CCCC1.O>[C:14]([O:13][C:11]([NH:10][CH:9]([CH2:8][O:20][Si:21]([C:34]([CH3:37])([CH3:36])[CH3:35])([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:18][OH:19])=[O:12])([CH3:15])([CH3:16])[CH3:17]

参加物

8

反応物 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 94078tert-ButyldiphenylchlorosilaneHCID 7019177N-Boc-L-serine methyl ester

生成物 1

HCID 227105032-(t-Butoxycarbonylamino)-3-(t-butyldiphenylsiloxy)propanol

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

At room temperature, imidazole (6.43 g) was added to a solution of N-(t-butoxycarbonyl)-L-serine methyl ester (13.8 g) in N,N-dimethylformamide (140 ml), followed by the addition of t-butyldiphenylsilyl chloride (19.7 ml) at 0° C. The resulting mixture was stirred at room temperature for 39 hours. Ethyl acetate (200 ml) and water (600 ml) were added to the reaction mixture to cause separation. The water layer was extracted with ethyl acetate (100 ml). The organic layers were combined, washed with saturated aqueous NaCl solution (100 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue thus obtained was dissolved in tetrahydrofuran (100 ml) and methanol (100 ml) without purification, followed by the addition of sodium borohydride (7.20 g) in portions at 0° C. After stirring at 0° C. for 2 hours and then at room temperature for 1 hour, ethyl acetate (100 ml), an aqueous saturated solution of ammonium chloride (300 ml) and water (300 ml) were added to the reaction mixture to cause separation. The water layer was extracted with ethyl acetate (100 ml). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue thus obtained was purified by chromatography on a silica gel column (500 g of silica gel, hexane:ethyl acetate=10:1˜1:1), whereby the title compound (24.9 g) was obtained as a white solid.

後処理

  1. customseparation
  2. extractionThe water layer was extracted with ethyl acetate (100 ml)
  3. washwashed with saturated aqueous NaCl solution (100 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue thus obtained
  7. custommethanol (100 ml) without purification
  8. additionfollowed by the addition of sodium borohydride (7.20 g) in portions at 0° C
  9. stirringAfter stirring at 0° C. for 2 hours
  10. waitat room temperature for 1 hour
  11. additionethyl acetate (100 ml), an aqueous saturated solution of ammonium chloride (300 ml) and water (300 ml) were added to the reaction mixture
  12. customseparation
  13. extractionThe water layer was extracted with ethyl acetate (100 ml)
  14. dry with materialdried over anhydrous sodium sulfate
  15. concentrationconcentrated under reduced pressure
  16. customThe residue thus obtained
  17. customwas purified by chromatography on a silica gel column (500 g of silica gel, hexane:ethyl acetate=10:1˜1:1), whereby the title compound (24.9 g)
  18. customwas obtained as a white solid

出典と根拠

ORDレコード
ord-d3b887741abe416e96692e58c47ff923
出典データセット
uspto-grants-2004_06
特許番号
US06747023B1

関連ノート

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