Hydrochloric Acid → HCID 53252467, compound

HRID 536609Notes

Reaction equation

HRID 536609 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19]COC)=[CH:15][CH:14]=3)=[CH:11][S:10][C:9]=2[CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[C:4]([O:28][CH3:29])[CH:3]=1.Cl>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=3)=[CH:11][S:10][C:9]=2[CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[C:4]([O:28][CH3:29])[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67255358HCID 67255358, compound

Product 1

HCID 53252467HCID 53252467, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(3-(4-chloro-2-methoxyphenyl)-4-(4-(methoxymethoxy)phenyl)thiophen-2-yl)propanoic acid (190 mg, 0.44 mmol) in THF (5 mL) was added HCl (1 mL, 12 M) and the mixture was stirred at room temperature for 2 hours. The mixture was diluted with water, extracted with EtOAc, and concentrated to give the crude compound, which was purified by preparative HPLC (Column: YMC ODS-AQ 150×30 cm, 5 μm; Retention Time: 15 min; Mobile phase: from 38% MeCN in water (0.05% TFA) to 68% MeCN in water (0.05% TFA); Wavelength: 220 nm, 254 nm; sample dissolved in DMSO) to give 3-(3-(4-chloro-2-methoxyphenyl)-4-(4-hydroxyphenyl)thiophen-2-yl)propanoic acid (47.5 mg, yield 28%). 1H NMR (CD3OD 400 MHz): δ 7.11 (s, 1H), 6.99 (d, J=1.6 Hz, 1H), 6.97-6.92 (m, 2H), 6.89 (d, J=8.4 Hz, 2H), 6.58 (d, J=8.8 Hz, 2H), 3.58 (s, 3H), 2.90 (t, J=8.0 Hz, 2H), 2.50 (t, J=8.0 Hz, 2H); MS (ESI): m/z [M+1]+=389.1.

Workup

  1. extractionextracted with EtOAc
  2. concentrationconcentrated
  3. customto give the crude compound, which
  4. customwas purified by preparative HPLC (Column: YMC ODS-AQ 150×30 cm, 5 μm; Retention Time: 15 min; Mobile phase: from 38% MeCN in water (0.05% TFA) to 68% MeCN in water (0.05% TFA); Wavelength: 220 nm, 254 nm; sample dissolved in DMSO)

Sources & evidence

ORD record
ord-ab9a29d978164ad992120ea9449ad5d0
Source dataset
uspto-grants-2014_10
Patent number
US08859611B2

Reaction notes

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