Hydrochloric Acid → (2R,5R)-2,5-dibenzyl-6-oxo-6-((R)-2-oxo-1-phenylazepan-3-ylamino)hexanoic acid

HRID 529455Notes

Reaction equation

HRID 529455 reaction equation
[CH2:1]([C@@H:8]([CH2:13][CH2:14][C@H:15]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:16](=[O:32])[NH:17][C@@H:18]1[CH2:24][CH2:23][CH2:22][CH2:21][N:20]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]1=[O:31])[C:9]([O:11]C)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-].O.Cl>CO>[CH2:1]([C@@H:8]([CH2:13][CH2:14][C@H:15]([CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:16](=[O:32])[NH:17][C@@H:18]1[CH2:24][CH2:23][CH2:22][CH2:21][N:20]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:19]1=[O:31])[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 86706191(2R,5R)-methyl 2,5-dibenzyl-6-oxo-6-((R)-2-oxo-1-phenylazepan-3-ylamino)hexanoate

Product 1

HCID 86706193(2R,5R)-2,5-dibenzyl-6-oxo-6-((R)-2-oxo-1-phenylazepan-3-ylamino)hexanoic acidYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a round bottom flask was added (2R,5R)-methyl 2,5-dibenzyl-6-oxo-6-((R)-2-oxo-1-phenylazepan-3-ylamino)hexanoate (300 mg, 0.570 mmol), 2 M LiOH in water (5.0 mL, 10 mmol) and MeOH (5 mL). The reaction was stirred at rt for 2 days. The reaction mixture was then cooled in an ice-bath and aqueous 1 M HCl was added slowly to adjust the pH to 4. A white precipitant was formed. The product was collected by filtration and washed with water (2×5 mL) to give (2R,5R)-2,5-dibenzyl-6-oxo-6-((R)-2-oxo-1-phenylazepan-3-ylamino)hexanoic acid (280 mg, 0.546 mmol, 96% yield) as a white solid. Anal. Calcd. for C32H36N2O4 m/z 512.4. found: 513.3 (M+H)+.

Workup

  1. temperatureThe reaction mixture was then cooled in an ice-bath
  2. customA white precipitant was formed
  3. filtrationThe product was collected by filtration
  4. washwashed with water (2×5 mL)

Sources & evidence

ORD record
ord-9ae84ef950d145e180cf59113f82b86b
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

Loading…