Lithium Hydroxide → HCID 71550896, compound

HRID 1261434Notes

Reaction equation

HRID 1261434 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([C:16](=[CH2:30])[CH2:17][CH2:18][NH:19][S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])(=[O:22])=[O:21])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:31])[CH:11]=2)[CH:6]=1.[Li+].[OH-]>C1COCC1.O>[Cl:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[S:20]([NH:19][CH2:18][CH2:17][C:16]([C:13]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:31])[CH:11]=2)[CH:6]=[C:5]([CH2:4][C:3]([OH:32])=[O:2])[C:14]=1[CH3:15])=[CH2:30])(=[O:21])=[O:22]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86683828HCID 86683828, compound

Product 1

HCID 71550896HCID 71550896, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {4-[3-(2-Chloro-benzenesulfonylamino)-1-methylene-propyl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (140 mg, 0.294 mmol) in THF (6 mL) was added a solution of LiOH (141 mg, 5.88 mmol) in water (1.5 mL). The resulting mixture was warmed with a heat gun to produce a clear solution, which was stirred for 15 hours at room temperature. At this time, LCMS analysis indicated the complete conversion of starting material. The THF was evaporated and the aqueous layer was diluted with water and slowly neutralized with 1.0 N HCl to obtain a white precipitate which was collected by filtration and washed with water and hexanes. After air drying, 125 mg of {4-[3-(2-chloro-benzenesulfonylamino)-1-methylene-propyl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid was isolated as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.43 (bs, 1H), 7.96 (t, J=5.6 Hz, 1H), 7.87-7.93 (m, 2H), 7.73 (s, 1H), 7.59-7.62 (m, 2H), 7.45-7.51 (m, 1H), 7.29-7.38 (m, 2H), 5.50 (dd, J=3.3, 1.2 Hz, 1H), 4.93 (d, J=1.0 Hz, 1.2H), 3.72-3.80 (m, 2H), 3.00-3.12 (m, 2H), 2.30-2.39 (m, 2H), 2.17 (s, 3H). MS cald. for C23H22ClFNO4S [(M+H)+] 462.1, obsd. 462.0.

Workup

  1. temperatureThe resulting mixture was warmed with a heat gun
  2. customto produce a clear solution, which
  3. customThe THF was evaporated
  4. additionthe aqueous layer was diluted with water and slowly neutralized with 1.0 N HCl
  5. customto obtain a white precipitate which
  6. filtrationwas collected by filtration
  7. washwashed with water and hexanes
  8. customAfter air drying

Sources & evidence

ORD record
ord-263f0b8f26a64601be46e15acff8c5ae
Source dataset
uspto-grants-2013_06
Patent number
US08470884B2

Reaction notes

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