tert-Butyl methyl ether → HCID 68593492, compound

HRID 1496840Notes

Reaction equation

HRID 1496840 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([C:7]([C:9]23[O:16][C:15](=[O:17])[CH:14]2[CH2:13][CH2:12][CH2:11][CH2:10]3)=[O:8])=[CH:5][CH:4]=1.[CH:20]([NH2:24])([CH2:22][CH3:23])C.[CH3:25]OC(C)(C)C>>[CH3:23][CH:22]([CH3:25])[CH2:20][NH:24][C:15]([CH:14]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1([OH:16])[C:7](=[O:8])[C:6]1[CH:18]=[CH:19][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:17]

Participants

4

Reactant 3

HCID 15413tert-Butyl methyl etherHCID 24874Sec-Butylamine2×HCID 86629708HCID 86629708, compound2×

Product 1

HCID 68593492HCID 68593492, compound

Procedure

20.8 g (0.08 mol) of 6-(4-methoxy-benzoyl)-7-oxa-bicyclo[4.2.0]octan-8-one (compound of example 10) are dissolved in 270 ml of tert-butyl methyl ether. 10.46 g (0.143 mol) of sec-butylamine are slowly added to this solution over one hour. The reaction mixture is stirred for 24 hours at room temperature. After this time, 1H-NMR analysis shows that the reaction mixture consists of 60% starting material and 40% of the product. Another 10.46 g (0.143 mol) of sec-butylamine are added and the reaction mixture is stirred for another four hours at room temperature. After that time the solvent is partially distilled off and substituted by the slow addition of 50 ml heptane. The precipitation formed is collected and the remaining liquid further diluted with hexane, resulting in the formation of an additional precipitation. The solids are collected and washed with hexane to give a white powder that according to 1H-NMR analysis consists of 64% product and 36% of the starting material. These compounds are separated by flash chromatography on silicagel (eluent: toluene/ethyl acetate 9:1), providing 2-hydroxy-2-(4-methoxy-benzoyl)-cyclohexanecarboxylic acid 2-methyl-propyl-amide as a colorless solid with a melting point of 143-147° C.

Workup

  1. stirringthe reaction mixture is stirred for another four hours at room temperature
  2. distillationAfter that time the solvent is partially distilled off
  3. additionsubstituted by the slow addition of 50 ml heptane
  4. customThe precipitation
  5. customformed
  6. customis collected
  7. additionthe remaining liquid further diluted with hexane
  8. customresulting in the formation of an additional precipitation
  9. customThe solids are collected
  10. washwashed with hexane
  11. customto give a white powder
  12. customThese compounds are separated by flash chromatography on silicagel (eluent: toluene/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-6803caed03c94338bc6ab109520442d3
Source dataset
uspto-grants-2015_12
Patent number
US09199934B2

Reaction notes

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