Water → HCID 178486043, Verbindung

HRID 25581Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 25581
[C:1]([O:5][C:6](=[O:19])[N:7]([C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]#[C:16][CH2:17][OH:18])[CH2:11][CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH3:20][S:21](Cl)(=[O:23])=[O:22].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][O:18][S:21]([CH3:20])(=[O:23])=[O:22])[CH2:13][CH2:14]1)=[O:19])([CH3:3])([CH3:2])[CH3:4]

Komponenten

7

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 178486040HCID 178486040, Verbindung

Produkt 1

HCID 178486043HCID 178486043, VerbindungAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 520 mg (1.95 mmol) of trans-[4-(3-Hydroxy-prop-1-ynyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester in 14 ml CH2Cl2 was treated at 0° C. with 0.17 ml (2.14 mmol) methanesulfonylchloride, 0.235 ml (2.92 mmol) pyridine and 238 mg (1.95 mmol) DMAP. The reaction mixture was warmed up over night to room temperature, water (2 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 435 mg (65%) of trans-Methanesulfonic acid 3-[4-(tert-butoxycarbonyl-methyl-amino)-cyclohexyl]-prop-2-ynyl ester, MS: 345 (M).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-793fb0110fba4dada34d375e4c77e623
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858651B2

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