Imidazole → methyl (2R)-2-{[(tert-butoxy)carbonyl]amino}-3-[(tert-butyldiphenylsilyl)oxy]propanoate

HRID 1711196

Reaktionsgleichung

Reaktionsgleichung von HRID 1711196
[CH3:1][O:2][C:3](=[O:15])[C@H:4]([NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5][OH:6].N1C=CN=C1.[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>C1COCC1>[CH3:1][O:2][C:3](=[O:15])[C@H:4]([NH:7][C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9])[CH2:5][O:6][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

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 377723N-Boc-D-serine methyl ester

Produkt 1

HCID 11762248methyl (2R)-2-{[(tert-butoxy)carbonyl]amino}-3-[(tert-butyldiphenylsilyl)oxy]propanoateAusbeute 72,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(R)-2-tert-Butoxycarbonylamino-3-hydroxy-propionic acid methyl ester (2.2 mg, 10 mmol) was dissolved in THF (20 ml). Imidazole (818 mg, 12 mmol) and TBDPS chloride (2.9 ml, 11 mmol) were added. The mixture was stirred at rt overnight. The mixture was then partitioned between CH2Cl2 and water (30 ml/30 ml). The organic layer was concentrated and the residue was purified by column chromatography (6/1, Hexanes/EtOAc) to give (R)-2-tert-butoxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-propionic acid methyl ester (3.3 g, 72%).

Aufarbeitung

  1. customThe mixture was then partitioned between CH2Cl2 and water (30 ml/30 ml)
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified by column chromatography (6/1, Hexanes/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-c430f316576c46f58d1614a10a8bcfcf
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790747B2

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