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Hydrochloric Acid → Ethyl 4-[2-(2-tert-butoxycarbonylaminoethyl)-5-isopropylphenoxy]butyrate

HRID 1351774
Notes
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Reaction equation

HRID 1351774 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17].C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32].Cl>CN(C)C=O>[C:16]([O:15][C:14]([NH:13][CH2:12][CH2:11][C:3]1[CH:4]=[CH:5][C:6]([CH:8]([CH3:9])[CH3:10])=[CH:7][C:2]=1[O:1][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:20])([CH3:18])([CH3:17])[CH3:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 18457008tert-butyl N-[2-(2-hydroxy-4-isopropylphenyl)ethyl]carbamate

Product 1

HCID 17856236Ethyl 4-[2-(2-tert-butoxycarbonylaminoethyl)-5-isopropylphenoxy]butyrate

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

tert-Butyl N-[2-(2-hydroxy-4-isopropylphenyl)ethyl]-carbamate (0.234 g) and 0.116 g of potassium carbonate were suspended in 5 mL of N,N-dimethylformamide. To the stirred suspension was added dropwise 0.126 mL of ethyl 4-bromobutyrate at room temperature, and the mixture was stirred at room temperature for 16 hours. To the reaction mixture were added 10 mL of 1 mol/L hydrochloric acid and then 20 mL of water, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane) to give 0.283 g of ethyl 4-[2-(2-tert-butoxycarbonylaminoethyl)-5-isopropylphenoxy]-butyrate.

Workup

  1. extraction20 mL of water, and the mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-fcb56d739416483694da9daa7f5a6d91
Source dataset
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07217832B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes