Phenylethanolamine → HCID 57495437, compound

HRID 1039152Notes

Reaction equation

HRID 1039152 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4].[CH3:11][O:12][C:13](=[O:23])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20](O)=[O:21].ON1C2C=CC=CC=2N=N1>C1COCC1.C(OCC)(=O)C>[CH3:11][O:12][C:13](=[O:23])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20](=[O:21])[NH:1][CH2:2][CH:3]([OH:4])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 1000PhenylethanolamineHCID 757711-HydroxybenzotriazoleHCID 5541918-Methoxy-8-oxooctanoic acid

Product 1

HCID 57495437HCID 57495437, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide(EDC) (8.5 g, 44.3 mL) to a solution of 2-amino-1-phenylethanol (5.0 g, 36.4 mmol), suberic acid monomethyl ester (6.85 g, 36.4 mmol) and 1-hydroxybenzotriazole (HOBt, 5.0 g, 37.0 mmol) in THF (200 mL) at room temperature under nitrogen. Stir the mixture for 12 hours. Dilute the mixture with ethyl acetate (600 mL), wash with 1N HCl (2×150 mL), brine (2×150 mL), NaHCO3 (2×150 mL) and brine (150 mL) solutions and dry over sodium sulfate. Remove the solvent under reduced pressure to provide 7-(2-hydroxy-2-phenylethylcarbamoyl)heptanoic acid methyl ester (10.3 g, 91%), which is used in the following step without purification.

Workup

  1. washwash with 1N HCl (2×150 mL), brine (2×150 mL), NaHCO3 (2×150 mL) and brine (150 mL) solutions
  2. dry with materialdry over sodium sulfate
  3. customRemove the solvent under reduced pressure

Sources & evidence

ORD record
ord-8041fb1d28a240a39846c15891d0bf10
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Reaction notes

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