Reaktion #640752

ord-f06fe5ff6da749bab460989d306cfb63

Reaktionsgleichung

Cc1ccc(S(=O)(=O)OCCO[C@@H]2CCC[C@H](OCc3nc(-c4cccc(C)c4)oc3C)C2)cc1
(1R,3S)-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]ethyl toluene-4-sulfonate
CCOC(=O)c1c(C)cccc1O
ethyl 2-hydroxy-6-methylbenzoate
[H-].[Na+]
sodium hydride
→
CCOC(=O)c1c(C)cccc1OCCO[C@@H]1CCC[C@H](OCc2nc(-c3cccc(C)c3)oc2C)C1
Ethyl (1R,3S)-2-methyl-6-{2-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]ethoxy}benzoate

Edukte

Cc1ccc(S(=O)(=O)OCCO[C@@H]2CCC[C@H](OCc3nc(-c4cccc(C)c4)oc3C)C2)cc1
(1R,3S)-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]ethyl toluene-4-sulfonate
CCOC(=O)c1c(C)cccc1O
ethyl 2-hydroxy-6-methylbenzoate
[H-].[Na+]
sodium hydride

Reagenzien

Keine

Lösungsmittel

[Cl-].[Na+]
NaCl
CCOC(C)=O
ethyl acetate
CN(C)C=O
DMF
CN(C)C=O
DMF

Reaktionsbedingungen

Temperatur
40°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturAfter cooling
  2. 2
    TrocknenThe organic phase is dried over sodium sulfate
  3. 3
    Sonstigethe solvent is removed under reduced pressure

Vorschrift

90 mg of ethyl 2-hydroxy-6-methylbenzoate are dissolved in 2 ml of dry DMF, and 23 mg of a 60 percent strength sodium hydride suspension are added. After 30 min at room temperature, 100 mg of ((1R,3S)-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]ethyl toluene-4-sulfonate in 2 ml of DMF are added. The mixture is stirred at 40° C. until the reaction has gone to completion (monitored by LC-MS). After cooling, the mixture is diluted with sat. NaCl solution and ethyl acetate. The organic phase is dried over sodium sulfate and the solvent is removed under reduced pressure. This gives ethyl (1R,3S)-2-methyl-6-{2-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]ethoxy}benzoate as a yellowish oil. C30H37NO6 (507.63), MS (ESI): 508 (M+H+).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08048901B2uspto-grants-2011_11