Hydrochloric Acid → 3-(5-(2-((4'-Chloro-[1,1'-biphenyl]-4-yl)carbamoyl)-5-methylphenyl)picolinamido)propanoic acid

HRID 405222Notes

Reaction equation

[OH-].[Na+].C1COCC1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:25]=3[C:31]3[CH:32]=[CH:33][C:34]([C:37]([NH:39][CH2:40][CH2:41][C:42]([O:44]CC)=[O:43])=[O:38])=[N:35][CH:36]=3)=[O:23])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1.Cl>CO>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:25]=3[C:31]3[CH:32]=[CH:33][C:34]([C:37]([NH:39][CH2:40][CH2:41][C:42]([OH:44])=[O:43])=[O:38])=[N:35][CH:36]=3)=[O:23])=[CH:17][CH:16]=2)=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 55 °C

Procedure

A 1M aqueous solution of NaOH (2.0 mL, 2.0 mmol) was added to a THF (1 mL) and MeOH (5 mL) solution of ethyl 3-(5-(2-((4′-chloro-[1,1′-biphenyl]-4-yl)carbamoyl)-5-methylphenyl)picolinamido)propanoate (50 mg, 0.09 mmol) and the resulting mixture was heated to 55° C. After 10 min the resulting mixture was neutralized with 2M aqueous HCl, concentrated and extracted with EtOAc. The combined extracts were concentrated and purified via column chromatography to yield the title compound.

Workup

concentrationconcentrated
extractionextracted with EtOAc
concentrationThe combined extracts were concentrated
custompurified via column chromatography

Sources & evidence

ORD record: ord-136f895b3c5c46edb300f2cca00f7cfe
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748624B2

Reaction notes

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