HCID 11555215, compound → HCID 23677045, compound

HRID 2244026Notes

Reaction equation

HRID 2244026 reaction equation
[C:1]([C:4]1[CH:30]=[CH:29][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([NH:19][C:20]3[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=3)[C:23]([OH:25])=[O:24])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[C:6]([CH2:31][CH2:32][CH3:33])[C:5]=1[OH:34])(=[O:3])[CH3:2].C(C(CCCC)C([O-])=O)C.[Na+:45]>C(OCC)(=O)C>[C:1]([C:4]1[CH:30]=[CH:29][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([NH:19][C:20]3[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=3)[C:23]([O-:25])=[O:24])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[C:6]([CH2:31][CH2:32][CH3:33])[C:5]=1[OH:34])(=[O:3])[CH3:2].[Na+:45]

Participants

4

Reactant 2

HCID 11555215HCID 11555215, compoundHCID 23672331Sodium 2-ethylhexanoate

Product 1

HCID 23677045HCID 23677045, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Stir 3-[4-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-benzenesulfonylamino]-benzoic acid (200 mg, 0.41 mmol) in ethyl acetate (10 mL) as a suspension. Add sodium 2-ethylhexanoate (92 mg, 0.90 mmol) in ethyl acetate (1 mL). After 12 hours at ambient temperature, concentrate the mixture under reduced pressure, sonicate the residue with ether (10 mL) and collect the title compound by filtration as a white solid (191 mg, 0.41 mmol): 1H NMR (DMSO-d6) δ 0.85 (t, 3H), 1.48 (m, 2H), 2.58 (m, 5H), 5.30 (s, 2H), 6.62 (d, 1H), 7.08 (m, 2H), 7.40 (m, 1H), 7.53 (m, 3H), 7.78 (m, 3H), 12.82 (s, 1H); MS (m/z): 482. (M−1).

Workup

  1. concentrationconcentrate the mixture under reduced pressure
  2. customsonicate the residue with ether (10 mL)
  3. customcollect the title compound

Sources & evidence

ORD record
ord-1d9f69f15f8a4ee48e3a7a4eff5c7e52
Source dataset
uspto-grants-2010_03
Patent number
US07678794B2

Reaction notes

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