Hydrochloric Acid → [(2-{3-[5-(2-Methoxymethyl-2'-methyl-biphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-ethyl)-methyl-amino]-acetic acid

HRID 2410596Notes

Reaction equation

HRID 2410596 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:16]=[C:17]([CH2:21][CH2:22][N:23]([CH3:32])[CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])[CH:18]=[CH:19][CH:20]=3)[N:11]=2)[CH:7]=[CH:6][C:5]=1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH3:39].Cl>O1CCOCC1>[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:16]=[C:17]([CH2:21][CH2:22][N:23]([CH2:24][C:25]([OH:27])=[O:26])[CH3:32])[CH:18]=[CH:19][CH:20]=3)[N:11]=2)[CH:7]=[CH:6][C:5]=1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH3:39]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 46940654tert-butyl N-[2-(3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethyl]-N-methylglycinate

Product 1

HCID 46940741[(2-{3-[5-(2-Methoxymethyl-2'-methyl-biphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-ethyl)-methyl-amino]-acetic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

To tert-butyl N-[2-(3-{5-[2-(methoxymethyl)-2′-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethyl]-N-methylglycinate (86 mg, 0.15 mmol) was added a 4N solution of HCl in dioxane and the mixture was heated in a tube at 70° C. for 3 hours. The solvent was then removed in vacuo and the residue was purified by preparative HPLC to give the title compound as a pale yellow oil. LC/MS (Method A): 472 (M+H)+, 470 (M−H)−. HPLC (Method K) Rt=18.0 min (Purity: 92.2%).

Workup

  1. customThe solvent was then removed in vacuo
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-b788c2349e5b415495b18cd1df75014c
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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