Methyl 1-bromocyclohexanecarboxylate → HCID 57718925, compound

HRID 1985249Notes

Reaction equation

HRID 1985249 reaction equation
[C:1]([C:5]1[CH:28]=[CH:27][C:8]([CH2:9][N:10]2[CH2:14][CH:13]([CH2:15][CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)[N:12]([CH3:25])[C:11]2=[O:26])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].Br[C:36]1([C:42]([O:44]C)=[O:43])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1>CC(O)(C)C>[C:1]([C:5]1[CH:28]=[CH:27][C:8]([CH2:9][N:10]2[CH2:14][CH:13]([CH2:15][CH2:16][CH2:17][C:18]3[CH:19]=[CH:20][C:21]([O:24][C:36]4([C:42]([OH:44])=[O:43])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]4)=[CH:22][CH:23]=3)[N:12]([CH3:25])[C:11]2=[O:26])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 3518593Methyl 1-bromocyclohexanecarboxylate2×HCID 23665647Potassium tert-butoxide2×HCID 68869042HCID 68869042, compound

Product 1

HCID 57718925HCID 57718925, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-(4-tert-butyl-benzyl)-4-[3-(4-hydroxy-phenyl)-propyl]-3-methyl-imidazolidin-2-one (0.074 g, 0.194 mmol) and potassium tert-butoxide (0.044 g, 0.392 nmol) in 2-methyl-2-propanol (8 mL) was heated to 60° C. under N2 and then and methyl 1-bromocyclohexanecarboxylate (0.274 g, 1.16 mmol) was added dropwise to the to 60° C. solution. Additional potassium tert-butoxide (0.044 g, 0.392 mmol) and methyl 1-bromocyclohexanecarboxylate (0.274 g, 1.16 mmol) was added to the reaction and it was stirred for 2 h. The reaction mixture was cooled and quenched with 1 N HCl. The mixture was then diluted with water and extracted with CH2Cl2. The organic layer was dried (Na2SO4) and the solvent removed in vacuo to afford 0.400 g of crude product that was purified by preparative HPLC to give 0.059 g (60%) 1-(4-{3-[1-(4-tert-butyl-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-propyl}-phenoxy)-cyclohexanecarboxylic acid. 1H NMR. HRMS (ES+) m/z exact mass calcd for C31H43N2O4 [M+1] 507.3223, found 507.3237.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customquenched with 1 N HCl
  3. additionThe mixture was then diluted with water
  4. extractionextracted with CH2Cl2
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. customthe solvent removed in vacuo
  7. customto afford 0.400 g of crude product that
  8. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-01264d5d617e4f56b5b63f3999b7fa48
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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