Hydrochloric Acid → HCID 56602331, compound

HRID 240264Notes

Reaction equation

HRID 240264 reaction equation
[Br:1][C:2]1[CH:28]=[C:27]([CH:29]([CH3:31])[CH3:30])[CH:26]=[CH:25][C:3]=1[O:4][CH:5]([CH3:24])[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([O:22][CH3:23])[CH2:16][C:17]([O:19]CC)=[O:18])=[CH:11][CH:10]=1)=[O:7].O.Cl>C(#N)C.[OH-].[Na+]>[Br:1][C:2]1[CH:28]=[C:27]([CH:29]([CH3:31])[CH3:30])[CH:26]=[CH:25][C:3]=1[O:4][CH:5]([CH3:24])[C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]([O:22][CH3:23])[CH2:16][C:17]([OH:19])=[O:18])=[CH:13][CH:14]=1)=[O:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 58031793HCID 58031793, compound

Product 1

HCID 56602331HCID 56602331, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 331 mg of ethyl 3-{4-[2-(2-bromo-4-isopropylphenoxy)propionylamino]-phenyl}-3-methoxypropionate in 7 ml of acetonitrile and 7 ml of 1 N NaOH (aq) was stirred at room temperature for 20 h. The reaction mixture was admixed with water and adjusted to pH=1 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 5 minutes 80% B→90% B). This gave 152 mg of 3-{4-[2-(2-bromo-4-isopropylphenoxy)propionylamino]phenyl}-3-methoxypropionic acid in 49% 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 5 minutes 80% B→90% B)

Sources & evidence

ORD record
ord-b8543fdcaa254c2594bbe22377ce798d
Source dataset
uspto-grants-2014_02
Patent number
US08648038B2

Reaction notes

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