Hydrochloric Acid → HCID 9844503, compound

HRID 1816015Notes

Reaction equation

HRID 1816015 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH:19]([C:24]3[S:25][C:26]([CH3:29])=[CH:27][N:28]=3)[CH2:20][C:21]([O-:23])=[O:22])=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=1.[OH-].[Na+].Cl>C1COCC1.O>[CH3:1][NH:2][C:3]1[N:8]=[C:7]([CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH:19]([C:24]3[S:25][C:26]([CH3:29])=[CH:27][N:28]=3)[CH2:20][C:21]([OH:23])=[O:22])=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86759667HCID 86759667, compound

Product 1

HCID 9844503HCID 9844503, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of methyl (±)-[4-[4-[2-(6-methylaminopyridin-2-yl)-1-ethoxy]phenyl]-3-(5-methylthiazol-2-yl)butanoate (0.85 mmole) in 1:1 THF/H2O (5 mL) was added 1.0 N NaOH (1.28 mL, 1.28 mmole). After 18 hr the mixture was acidified to pH 6 using 10% HCl then concentrated to dryness. The residue was chromatographed on silica gel (EtOH) to give the title compound as a yellow solid (217 mg, 62% over 2 steps). MS (ES) m/e 412 (M+H)+. Anal. Calcd for C22H25N3O3S 1.2H2O: C, 61.01; H. 6.38; N. 9.70. Found: C, 61.25; H. 6.06; N, 9.32.

Workup

  1. concentrationthen concentrated to dryness
  2. customThe residue was chromatographed on silica gel (EtOH)

Sources & evidence

ORD record
ord-1a4f34071de1453a810281f9a3bf4ed8
Source dataset
uspto-grants-2005_04
Patent number
US06881736B1

Reaction notes

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