Hydrochloric Acid → [3-((2R)-2-{[(1R)-1-Phenylethyl]amino}propyl)phenyl]acetic acid

HRID 1866564Notes

Reaction equation

HRID 1866564 reaction equation
[OH-].[Li+].Cl.C[O:5][C:6](=[O:26])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][C@H:15]([NH:17][C@@H:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH3:19])[CH3:16])[CH:9]=1.Cl>CO>[C:20]1([C@H:18]([NH:17][C@H:15]([CH3:16])[CH2:14][C:10]2[CH:9]=[C:8]([CH2:7][C:6]([OH:26])=[O:5])[CH:13]=[CH:12][CH:11]=2)[CH3:19])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 46938908methyl[3-((2R)-2-{[(1R)-1-phenyl-ethyl]-amino}-propyl)-phenyl]-acetate hydrochloride

Product 1

HCID 58907418[3-((2R)-2-{[(1R)-1-Phenylethyl]amino}propyl)phenyl]acetic acidYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Lithium hydroxide solution (1M in water, 90 mL, 90 mmol) was added to a solution of methyl[3-((2R)-2-{[(1R)-1-phenyl-ethyl]-amino}-propyl)-phenyl]-acetate hydrochloride (preparation 26), (13.5 g, 43.5 mmol) in methanol (200 mL) and the mixture was stirred at room temperature for 18 hours. 1M Hydrochloric acid (90 mL) was then added to the reaction mixture and the methanol removed in vacuo. The resulting precipitate was filtered off and washed with water (20 mL) and a mixture of ethanol/diethyl ether, 20:80, to afford the title compound as a solid in 91% yield, 11.8 g 1H NMR (400 MHz, CD3OD) δ: 7.52-7.45 (5H, m), 7.22-7.18 (2H, m), 7.19 (1H, s), 6.92 (1H, d), 4.56-4.48 (1H, q), 3.46 (2H, s), 3.26-3.13 (2H, m), 2.66-2.62 (1H, m), 1.62 (3H, d), 1.16 (3H, d) ppm; LRMS ESI m/z 298 [M+H]+

Workup

  1. customthe methanol removed in vacuo
  2. filtrationThe resulting precipitate was filtered off
  3. washwashed with water (20 mL)
  4. additiona mixture of ethanol/diethyl ether, 20:80

Sources & evidence

ORD record
ord-06c390cc73a9407485da74ab8b144ecc
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

Loading…