Hydrochloric Acid → 2-[n-Methyl-n-((r/s)-alpha-methyl-4-benzyloxyphenylacetyl)amino]-(r)-propionic acid

HRID 843394Notes

Reaction equation

HRID 843394 reaction equation
[CH3:1][N:2]([C@H:21]([CH3:26])[C:22]([O:24]C)=[O:23])[C:3](=[O:20])[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][CH:7]=1)[CH3:5].[Li+].[OH-].Cl.CCOC(C)=O>C1COCC1>[CH3:1][N:2]([C@H:21]([CH3:26])[C:22]([OH:24])=[O:23])[C:3](=[O:20])[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][CH:7]=1)[CH3:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 69882983Methyl 2-[n-methyl-n-((r/s)-alpha-methyl-4-benzyloxyphenylacetyl)amino]-(r)-propionate

Product 1

HCID 698838482-[n-Methyl-n-((r/s)-alpha-methyl-4-benzyloxyphenylacetyl)amino]-(r)-propionic acidYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-[N-methyl-N-((R/S)-α-methyl-4-benzyloxyphenylacetyl)amino]-(R)-propionate 45c (380 mg, 1.1 mmol) in THF (10 mL) was added 1 N LiOH (2 mL). The solution was stirred for 1 h and acidified with 1 N HCl to pH 3. EtOAc was added and the organic layer was separated, washed with brine, dried (MgSO4) and concentrated to afford the carboxylic acid (360 mg, 98%) as a solid. MS (CI—NH3): (M+H)+=342.

Workup

  1. customthe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-be4e7211b0224c1395fbad7025c7a46d
Source dataset
uspto-grants-2002_04
Patent number
US06376665B1

Reaction notes

Loading…