Hydrochloric Acid → HCID 56602332, compound

HRID 240266Notes

Reaction equation

HRID 240266 reaction equation
[CH:1]([C:4]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:5]=1[O:6][CH:7]([CH3:26])[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([O:24][CH3:25])[CH2:18][C:19]([O:21]CC)=[O:20])=[CH:13][CH:12]=1)=[O:9])([CH3:3])[CH3:2].O.Cl>[OH-].[Na+].C1COCC1.[OH-].[Na+]>[CH:1]([C:4]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:5]=1[O:6][CH:7]([CH3:26])[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([O:24][CH3:25])[CH2:18][C:19]([OH:21])=[O:20])=[CH:13][CH:12]=1)=[O:9])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 58031818HCID 58031818, compound

Product 1

HCID 56602332HCID 56602332, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 86660761HCID 86660761, compoundSolvent

Procedure

A solution of 287 mg (0.67 mmol) of ethyl 3-{4-[2-(2-isopropyl-5-methylphenoxy)-propionylamino]phenyl}-3-methoxypropionate in 10 ml of 2N NaOH/THF/NaOH in a ratio of 1:1:1 was left to stand at RT for 30 minutes. The reaction mixture was admixed with water and adjusted to pH=6-7 with 1 N HCl (aq) and then extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered and concentrated under high vacuum. The crude mixture was purified by means of preparative HPLC (Merck Hibar Purospher Star RP-18e 10 μm 25×250 mm; A: H2O+0.05% TFA; B: ACN+0.05% TFA; flow rate: 50 ml/min; in 10 minutes 10% B→80% B; in 10 minutes 80% B→90% B). This gave 138 mg of 3-{4-[2-(2-isopropyl-5-methylphenoxy)propionylamino]phenyl}-3-methoxypropionic acid in 51% yield over the two stages.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under high vacuum
  5. customThe crude mixture was purified by means of preparative HPLC (Merck Hibar Purospher Star RP-18e 10 μm 25×250 mm
  6. waitin 10 minutes 10% B→80% B
  7. waitin 10 minutes 80% B→90% B)

Sources & evidence

ORD record
ord-8cf73f4c6fbf4034a4d1e2375cc25858
Source dataset
uspto-grants-2014_02
Patent number
US08648038B2

Reaction notes

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