Ethyl chloroformate → HCID 66818628, compound

HRID 1024773Notes

Reaction equation

HRID 1024773 reaction equation
[C:1]([O:5][C:6](=[O:33])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:32])[C:16]2[CH:21]=[C:20]([OH:22])[CH:19]=[C:18]([O:23][C:24]3[CH:29]=[CH:28][C:27]([CH2:30][NH2:31])=[CH:26][CH:25]=3)[CH:17]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:36]([O:38][C:39](Cl)=[O:40])[CH3:37]>C1COCC1>[C:1]([O:5][C:6](=[O:33])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:32])[C:16]2[CH:21]=[C:20]([OH:22])[CH:19]=[C:18]([O:23][C:24]3[CH:29]=[CH:28][C:27]([CH2:30][NH:31][C:39]([O:38][CH2:36][CH3:37])=[O:40])=[CH:26][CH:25]=3)[CH:17]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 24758Sodium hydrideHCID 66818730HCID 66818730, compound

Product 1

HCID 66818628HCID 66818628, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 1.0 g (2.19 mmol) of {4-[3-(4-aminomethyl-phenoxy)-5-hydroxy-benzoyl-amino]-cyclohexyl}-carbamic acid tert-butyl ester, dissolved in 5 ml of THF, 0.13 g (5.47 mmol) of sodium hydride was added at 0° C. and the mixture was stirred for 15 min at same temperature. 0.26 g (2.40 mmol) of ethylchloroformate, dissolved in 2 ml of THF, was added dropwise to the stirred solution during 10 min and then the reaction mixture was stirred at RT for 6 h. After reaction completion, solvent was removed under reduced pressure and the obtained residue was dissolved in 200 ml of ethyl acetate. Organic layer was washed with (3×100 ml) of brine followed by water (2×100 ml). Organic phase was dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 0.56 g of required product which was used for the next step witout further purification. Percentage purity (LCMS): 59.7%, (M+1)=527.2+1.

Workup

  1. additionwas added dropwise to the stirred solution during 10 min
  2. stirringthe reaction mixture was stirred at RT for 6 h
  3. customAfter reaction completion, solvent
  4. customwas removed under reduced pressure
  5. dissolutionthe obtained residue was dissolved in 200 ml of ethyl acetate
  6. washOrganic layer was washed with (3×100 ml) of brine
  7. dry with materialOrganic phase was dried over anhydrous sodium sulphate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7bcc35e1dc634a4dade13fe40e1ab32e
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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