Triethylamine → Methanesulfonic acid (S)-2-tert-butoxycarbonylamino-4,4-dimethyl-pentyl ester
Reaktionsgleichung
[C:1]([O:5][C:6](=[O:16])[NH:7][C@H:8]([CH2:14][OH:15])[CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[S:24](Cl)([CH3:27])(=[O:26])=[O:25]>C(Cl)Cl>[C:1]([O:5][C:6]([NH:7][C@@H:8]([CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:14][O:15][S:24]([CH3:27])(=[O:26])=[O:25])=[O:16])([CH3:4])([CH3:2])[CH3:3]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of ((S)-1-hydroxymethyl-3,3-dimethyl-butyl)-carbamic acid tert-butyl ester (250 mg, 0.756 mmol) and triethylamine (0.116 mL, 0.832 mmol) in CH2Cl2 (4 mL) cooled at −10° C. was added under nitrogen atmosphere mesylchloride (0.065 mL, 0.832 mmol) and the reaction mixture was stirred at 0° C. for 1.5 h. The reaction mixture was quenched with ice and water then extracted twice with EtOAc. The combined organic layers were washed with water, dried (Na2SO4), filtered and concentrated. The crude material (colorless oil) was used without purification in the next step. TLC, Rf (c-hexane/EtOAc 1:1): 0.46.
Aufarbeitung
- customThe reaction mixture was quenched with ice and water
- extractionthen extracted twice with EtOAc
- washThe combined organic layers were washed with water
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- customThe crude material (colorless oil) was used without purification in the next step
Quellen und Nachweise
- ORD-Eintrag
- ord-00bee42ab69b492c8fde03c83b3525ca
- Quelldatensatz
- uspto-grants-2016_07
- Patentnummer
- US09388199B2
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