1-Hydroxybenzotriazole → 2-(acetylamino)-3-(4-bromophenyl)-N-(2-hydroxy-4,4-dimethylhexyl)propanamide

HRID 425400Notes

Reaction equation

HRID 425400 reaction equation
C(=O)(O)[O-].[Na+].[C:6]([NH:9][CH:10]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=1)[C:11]([OH:13])=O)(=[O:8])[CH3:7].[NH2:22][CH2:23][CH:24]([OH:31])[CH2:25][C:26]([CH3:30])([CH3:29])[CH2:27][CH3:28].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>C(Cl)Cl>[C:6]([NH:9][CH:10]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=1)[C:11]([NH:22][CH2:23][CH:24]([OH:31])[CH2:25][C:26]([CH3:30])([CH3:29])[CH2:27][CH3:28])=[O:13])(=[O:8])[CH3:7]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 5172487AC-P-Bromo-DL-phe-OHHCID 55289824HCID 55289824, compound

Product 1

HCID 667058552-(acetylamino)-3-(4-bromophenyl)-N-(2-hydroxy-4,4-dimethylhexyl)propanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sodium bicarbonate (7.05 g, 83.8 mmol) was added to an ambient temperature solution of 2-(acetylamino)-3-(4-bromophenyl)propanoic acid (3 g, 10.5 mmol), 1-amino-4,4-dimethylhexan-2-ol (3.04 g, 21.0 mmol), 1-[3-(dimethylamino) propyl]-3-ethylcarbodiimide hydrochloride (4.02 g, 21.0 mmol) and 1-hydroxybenzotriazole (2.83 g, 21.0 mmol) in methylene chloride (105 mL). After stirring at ambient temperature overnight, the reaction mixture was quenched with water and extracted with methylene chloride and ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-100% acetone/methylene chloride afforded 2-(acetylamino)-3-(4-bromophenyl)-N-(2-hydroxy-4,4-dimethylhexyl)propanamide.

Workup

  1. customthe reaction mixture was quenched with water
  2. extractionextracted with methylene chloride and ethyl acetate
  3. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bee873f249034be2987f610bf044608e
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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