Water → HCID 178486037, Verbindung

HRID 2057319Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2057319
[C:1]([O:5][C:6](=[O:20])[N:7]([C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]#[C:16][CH2:17][CH2:18][OH:19])[CH2:11][CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH3:21][S:22](Cl)(=[O:24])=[O:23].N1C=CC=CC=1.O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6]([N:7]([CH3:8])[C@H:9]1[CH2:10][CH2:11][C@H:12]([C:15]#[C:16][CH2:17][CH2:18][O:19][S:22]([CH3:21])(=[O:24])=[O:23])[CH2:13][CH2:14]1)=[O:20])([CH3:3])([CH3:2])[CH3:4]

Komponenten

7

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 178486035HCID 178486035, Verbindung

Produkt 1

HCID 178486037HCID 178486037, VerbindungAusbeute 105,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 2.66 g (9.44 mmol) of trans-[4-(4-Hydroxy-but-1-ynyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester in 75 ml CH2Cl2 was treated at 0° C. with 0.81 ml (10.38 mmol) methanesulfonylchloride, 1.14 ml (14.16 mmol) pyridine and 1.15 g (9.44 mmol) DMAP. The reaction mixture was stirred at RT for 3 h, water (19 ml) was added and the reaction was stirred for 5 min. After extraction with aqueous 10% KHSO4/Et2O (3×) the organic phases were washed with aqueous saturated NaHCO3 (2×), aqueous 10% NaCl, dried over Na2SO4 and evaporated to yield 3.57 g (quantitative) of trans-Methanesulfonic acid 4-[4-(tert-butoxycarbonyl-methyl-amino)-cyclohexyl]-but-3-ynyl ester, MS: 360 (MH+).

Aufarbeitung

  1. stirringthe reaction was stirred for 5 min
  2. extractionAfter extraction with aqueous 10% KHSO4/Et2O (3×) the organic phases
  3. washwere washed with aqueous saturated NaHCO3 (2×), aqueous 10% NaCl
  4. dry with materialdried over Na2SO4
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-58615ff07f9d4746956ccfc2d43807e9
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07335687B2

Notizen zur Reaktion

Wird geladen…