Triethylamine → 2-(Benzyloxycarbonylamino)-3-(1-methylcyclohexyl)propyl methanesulfonate
Reaktionsgleichung
[OH:1][CH2:2][CH:3]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:4][C:5]1([CH3:11])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>C(Cl)Cl>[CH3:30][S:31]([O:1][CH2:2][CH:3]([NH:12][C:13]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:22])[CH2:4][C:5]1([CH3:11])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1)(=[O:33])=[O:32]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
A mixture of 0.3607 g (1.18 mmol) of benzyl 1-hydroxy-3-(1-methylcyclohexyl)propan-2-ylcarbamate, 0.4 mL (2.87 mmol, 2.43 equiv) of triethylamine, 0.1 mL (1.29 mmol, 1.09 equiv) of methanesulfonyl chloride in CH2Cl2 (10 mL) was stirred at 0° C. for 1.5 h. The reaction mixture was quenched with ice water, extracted with CH2Cl2, washed with aqueous NaHCO3, and dried over Na2SO4. After the solvent was removed in vacuo, the crude 2-(benzyloxycarbonylamino)-3-(1-methylcyclohexyl)propyl methanesulfonate was used directly in the next step without further purification. MS ESI +ve m/z 406 (M+Na).
Aufarbeitung
- customThe reaction mixture was quenched with ice water
- extractionextracted with CH2Cl2
- washwashed with aqueous NaHCO3
- dry with materialdried over Na2SO4
- customAfter the solvent was removed in vacuo
- customthe crude 2-(benzyloxycarbonylamino)-3-(1-methylcyclohexyl)propyl methanesulfonate was used directly in the next step without further purification
Quellen und Nachweise
- ORD-Eintrag
- ord-955a3d1e77ea42498895707e1b154213
- Quelldatensatz
- uspto-grants-2013_07
- Patentnummer
- US08487108B2
Notizen zur Reaktion
Wird geladen…