Triethylamine → HCID 11202011, Verbindung

HRID 1173006

Reaktionsgleichung

Reaktionsgleichung von HRID 1173006
[CH:1]([C:4]1[N:5]=[C:6]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[S:7][C:8]=1[CH2:9]O)([CH3:3])[CH3:2].CCN(CC)CC.CS(Cl)(=O)=O.[NH2:33][C:34]1[CH:39]=[CH:38][C:37]([C@@H:40]2[CH2:42][C@H:41]2[C:43]([OH:45])=[O:44])=[CH:36][CH:35]=1>ClCCl.O>[CH:1]([C:4]1[N:5]=[C:6]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[S:7][C:8]=1[CH2:9][NH:33][C:34]1[CH:35]=[CH:36][C:37]([C@@H:40]2[CH2:42][C@H:41]2[C:43]([OH:45])=[O:44])=[CH:38][CH:39]=1)([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 587657624-Isopropyl-2-[4-(trifluoromethyl)phenyl]thiazole-5-methanolHCID 68668314(1R,2R)-2-(4-aminophenyl)cyclopropane-1-carboxylic acid

Produkt 1

HCID 11202011HCID 11202011, VerbindungAusbeute 19,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of {(4-isopropyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methanol (0.10 g, 0.331 mmol) in dichloromethane (3 mL) was added Et3N (0.04 g, 0.39 mmol) and the mixture cooled to 0° C. The mixture stirred for 15 min after which methanesulfonyl chloride (0.04 g, 0.36 mmol) was added followed 30 min later by the addition of racemic-(trans)-2-(4-aminophenyl)cyclopropanecarboxylic acid (I-1) (0.09 g, 0.49 mmol). The solution stirred for 24 h after which it was poured into H2O, the organics extracted with dichloromethane, dried over MgSO4, and the solvents reduced in vacuo. The crude material was purified on silica gel eluting with an increasing gradient from hexanes to 30% ethyl acetate/hexanes to give the title compound as a yellow powder (0.03 g, 16%). 1H NMR (400 MHz, CDCl3) δ 8.01 (d, J=8.3 Hz, 2H), 7.65 (d, J=8.2 Hz, 2H), 6.98 (d, J=8.4 Hz, 2H), 6.62 (d, J=8.6 Hz, 2H), 4.47 (s, 2H), 3.50-3.47 (m, 1H), 3.18-3.15 (m, 1H), 2.53-2.51 (m, 1H), 1.80-1.77 (m, 1H), 1.61-1.58 (m, 1H), 1.37-1.26 (m, 7H).

Aufarbeitung

  1. additionwas added
  2. extractionthe organics extracted with dichloromethane
  3. dry with materialdried over MgSO4
  4. customThe crude material was purified on silica gel eluting with an increasing gradient from hexanes to 30% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-ee78b6a53a9e4997a25bbcdb804911dd
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834013B2

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