4-tert-Butylcyclohexyl chloroformate → HCID 21365027, compound

HRID 987296Notes

Reaction equation

HRID 987296 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C@H:19]([O:23][CH2:24][CH3:25])[C:20]([OH:22])=[O:21])=[CH:14][CH:13]=2)=[CH:5][CH:4]=1.C(=O)([O-])O.[Na+].Cl[C:32]([O:34][CH:35]1[CH2:40][CH2:39][CH:38]([C:41]([CH3:44])([CH3:43])[CH3:42])[CH2:37][CH2:36]1)=[O:33].CO.ClCCl>O1CCCC1>[CH2:24]([O:23][C@@H:19]([CH2:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH2:9][C:6]2[CH:5]=[CH:4][C:3]([NH:2][C:32]([O:34][CH:35]3[CH2:40][CH2:39][CH:38]([C:41]([CH3:44])([CH3:43])[CH3:42])[CH2:37][CH2:36]3)=[O:33])=[CH:8][CH:7]=2)=[CH:13][CH:14]=1)[C:20]([OH:22])=[O:21])[CH3:25]

Participants

6

Reactant 4

HCID 1706084-tert-Butylcyclohexyl chloroformate2×HCID 516892Sodium BicarbonateHCID 21226129Dichloromethane methanolHCID 86595065HCID 86595065, compound

Product 1

HCID 21365027HCID 21365027, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-{4-[2-(4-Aminophenyl)ethoxy]phenyl}-(S)-2-ethoxypropanoic acid hydro chloride (0.2 g, 0.547 mmole) and sodium hydrogen carbonate (0.05 g, 0.595 mmole) were mixed in tetrahydrofurane (5 ml), stirred at room temperature for 20 minutes and then 4-tert-butylcyclohexyl chloroformate (0.131 g, 0.599 mmole) was added. The reaction mixture was stirred at room temperature overnight and then a little more 4-tert-butylcyclohexyl chloroformate was added since the reaction was not complete according to HPLC. The reaction mixture was stirred for 2 more hours and then evaporated to dryness. Ethyl acetate and water were added to the residue and the phases were separated. The organic phase was dried with magnesium sulfate and the solvent was evaporated. Chromatography on silica gel (Isolute, SI ) using dichloromethane:heptane (1:1), followed by dichloromethane, and then methanol: dichloromethane (1:99) as eluants gave 0.28 g (93% yield) (S)-2-ethoxy-3[4-(2-[4-([{4-(tert-butyl)cyclohexyl}oxy]carbonylamino)phenyl]ethoxy)phenyl]propanoic acid.

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. stirringThe reaction mixture was stirred for 2 more hours
  3. customevaporated to dryness
  4. additionEthyl acetate and water were added to the residue
  5. customthe phases were separated
  6. dry with materialThe organic phase was dried with magnesium sulfate
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-70b93e59508a49c4b9a96e87416f5c57
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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