Hydrochloric Acid → (R)-2-[2,6-Dibromo-4-(dibenzothiophen-1-yl)-phenoxy]-3-phenyl-propionic acid

HRID 611743Notes

Reaction equation

HRID 611743 reaction equation
[OH-].[K+].C[O:4][C:5](=[O:36])[C@H:6]([O:14][C:15]1[C:20]([Br:21])=[CH:19][C:18]([C:22]2[C:30]3[C:29]4[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=4[S:27][C:26]=3[CH:25]=[CH:24][CH:23]=2)=[CH:17][C:16]=1[Br:35])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl>C1COCC1.CO.O>[Br:35][C:16]1[CH:17]=[C:18]([C:22]2[C:30]3[C:29]4[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=4[S:27][C:26]=3[CH:25]=[CH:24][CH:23]=2)[CH:19]=[C:20]([Br:21])[C:15]=1[O:14][C@H:6]([CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:5]([OH:36])=[O:4]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 54334532(R)-2-[2,6-Dibromo-4-(dibenzothiophen-1-yl)-phenoxy]-3-phenyl-propionic acid methyl ester

Product 1

HCID 54226343(R)-2-[2,6-Dibromo-4-(dibenzothiophen-1-yl)-phenoxy]-3-phenyl-propionic acidYield 80%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.0 N Aqueous potassium hydroxide (0.81 mL, 0.81 mmol) was added to a stirred solution of (R)-2-[2,6-dibromo-4-(dibenzothiophen-1-yl)-phenoxy]-3-phenyl-propionic acid methyl ester (0.242 g, 0.406 mmol) in THF (4 mL) and methanol (2.5 mL). After 1.5 h at ambient temperature, the reaction mixture was diluted with water, acidified with 10% aqueous HCl and filtered. The solid was washed with water and triturated with pet. ether. The solid was dried in vacuo at 70° C. to provide the title compound as a white solid (0.190, 80%): [a]D25=+19.73 (10.14 mg/mL CHCl3); NMR (CDCl3): δ 7.89 (dd, J=8, 1 Hz, 1H), 7.83 (ddd., J=8, 1, 1 Hz, 1H), 7.63 (d, J=2 Hz, 1H), 7.62 (d, J=2 Hz, 1H), 7.45 (dd, J=8, 6 Hz, 2H), 7.41-7.154 (m, 8H), 5.33 (t, J=8 Hz, 1H), 3.54 (dd, J=5, 2 Hz, 1H), 3.52 (dd, J=8, 4 Hz, 1H); MS (EI): [M+], 2 bromine isotope pattern, 580 (20%), 582 (40%) 584 (25%); Anal. Calc. for C27H18Br2O3S: C, 55.69, H, 3.11, N, 0.00. Found: C, 55.23, H, 2.97, N, 0.07; Analytical HPLC :98.8%.

Workup

  1. filtrationfiltered
  2. washThe solid was washed with water
  3. customtriturated with pet. ether
  4. customThe solid was dried in vacuo at 70° C.

Sources & evidence

ORD record
ord-ed7a6ccb1e5045a5972fdc4e5e9155a5
Source dataset
uspto-grants-1999_12
Patent number
US06001867

Reaction notes

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