Tyrosine Methyl Ester → O-(tert-butyldiphenylsilyl)-L-tyrosine methyl ester

HRID 850142

Reaktionsgleichung

Reaktionsgleichung von HRID 850142
[CH3:1][O:2][C:3](=[O:14])[C@H:4]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[NH2:5].C(N(C(C)C)CC)(C)C.[Si:24](Cl)([C:37]([CH3:40])([CH3:39])[CH3:38])([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:14])[C@H:4]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][Si:24]([C:37]([CH3:40])([CH3:39])[CH3:38])([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:11][CH:12]=1)[NH2:5]

Komponenten

5

Edukt 3

HCID 70652Tyrosine Methyl EsterHCID 81531DiisopropylethylamineHCID 94078tert-Butyldiphenylchlorosilane

Produkt 1

HCID 53905505O-(tert-butyldiphenylsilyl)-L-tyrosine methyl esterAusbeute 87,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of L-tyrosine methyl ester (Sigma Chemical Company) (10.0 g, 51.3 mmol) and diisopropylethylamine (25.9 g, 200.0 mmol) in CH2Cl2 (400 mL) was added t-butyldiphenylsilyl chloride (TBDPS-Cl; 35.2 g, 128.2 mmol) at 23° C. The resultant mixture was stirred at 23° C. for 14 hours. The crude reaction mixture was dried over (MgSO4) and concentrated in vacuo. The resultant residue was purified by silica gel flash column chromatography. The polarity of the eluting solvent mixture was adjusted according to the Rf value of the product. The eluted fractions were combined, dried over MgSO4, concentrated and dried to give 19.5 g (87.8% yield) of O-(tert-butyldiphenylsilyl)-L-tyrosine methyl ester as a colorless syrup. Rf (hexanes/ethyl acetate (AcOEt)/methanol (MeOH) 20:20:1)=0.38.

Aufarbeitung

  1. customThe crude reaction mixture
  2. dry with materialwas dried over (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe resultant residue was purified by silica gel flash column chromatography
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-87039577dfd94d8998a5be8198a65934
Quelldatensatz
uspto-grants-2000_01
Patentnummer
US06015887

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