Pyridine → (S)-2-(tert-butoxycarbonylamino)-1-cyclohexylpentan-3-yl 4-methylbenzenesulfonate

HRID 451769Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 451769
[CH:1]1([CH2:7][C@H:8]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:9]([OH:12])[CH2:10][CH3:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.[S:27](Cl)([C:30]1[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=1)(=[O:29])=[O:28]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:34][C:33]1[CH:35]=[CH:36][C:30]([S:27]([O:12][CH:9]([CH2:10][CH3:11])[C@@H:8]([NH:13][C:14]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:20])[CH2:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)(=[O:29])=[O:28])=[CH:31][CH:32]=1

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 59201568(S)-tert-butyl 1-cyclohexyl-3-hydroxypentan-2-ylcarbamate

Produkt 1

HCID 59201516(S)-2-(tert-butoxycarbonylamino)-1-cyclohexylpentan-3-yl 4-methylbenzenesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of (S)-tert-butyl 1-cyclohexyl-3-hydroxypentan-2-ylcarbamate (1.067 g, 3.74 mmol), catalytic amount of DMAP, and pyridine (0.651 g, 8.24 mmol) at 0° C. was added TsCl (0.856 g, 4.49 mmol) in CH2Cl2 (4 mL) over 2 min. The resulting solution was stirred at rt overnight. The reaction mixture was diluted with EtoAc, washed with 1 M HCl, sat. aq. NaHCO3, brine, dried over Na2SO4 and filtered. The filtrate was concentrated and purified by on silica gel chromatography to give (S)-2-(tert-butoxycarbonylamino)-1-cyclohexylpentan-3-yl 4-methylbenzenesulfonate as a white solid. MS ESI +ve m/z 462 (M+Na).

Aufarbeitung

  1. additionThe reaction mixture was diluted with EtoAc
  2. washwashed with 1 M HCl, sat. aq. NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified by on silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8854310ef19d428a93c7bd15b5ffc3a5
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08487108B2

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