Lithium hydroxide, monohydrate → HCID 71711508, compound

HRID 1468431Notes

Reaction equation

HRID 1468431 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:34])[CH2:7][C:8]1[C:17]([CH3:18])=[C:16]([C:19]2[CH:24]=[CH:23][C:22]([S:25]([N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)(=[O:27])=[O:26])=[CH:21][CH:20]=2)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([F:33])[CH:14]=2)[CH:9]=1.C1COCC1.O>CCCCCC>[F:33][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH2:7][C:6]([OH:34])=[O:5])[C:17]([CH3:18])=[C:16]2[C:19]1[CH:20]=[CH:21][C:22]([S:25]([N:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)(=[O:26])=[O:27])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 21881883Oxolane--water (1/1)HCID 86695018HCID 86695018, compound

Product 1

HCID 71711508HCID 71711508, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Lithium hydroxide monohydrate (0.02 g, 0.68 mmol) was added to a stirred solution of {6-fluoro-3-methyl-4-[4-(pyrrolidine-1-sulfonyl)-phenyl]-naphthalen-2-yl}-acetic acid methyl ester (0.075 g, 0.17 mmol) in a 3:1 mixture of THF—H2O mixture (8 mL). The reaction mixture was stirred for 16 hours at room temperature. The reaction mixture was concentrated to remove THF, and the crude material was diluted with water, acidified [pH˜2] with a 6 N aqueous solution of hydrochloric acid. The mixture was extracted twice with ethyl acetate. The collected organic layers were washed with water and brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to give the crude product. Trituration with hexane afforded {6-fluoro-3-methyl-4-[4-(pyrrolidine-1-sulfonyl)-phenyl]-naphthalen-2-yl}-acetic acid (0.064 g, 88%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.47 (br. s, 1 H), 7.98 (d, J=8.31 Hz, 3H), 7.91 (s, 1 H), 7.51 (d, J=8.31 Hz, 2 H), 7.39 (td, J=8.80, 2.40 Hz, 1 H), 6.69 (dd, J=11.20, 2.40 Hz, 1 H), 3.85 (s, 2 H), 3.21-3.29 (m, 4 H), 2.07 (s, 3 H), 1.64-1.76 (m, 4 H). MS calcd. for C23H21FNO4S [(M−H)−] 426, obsd. 426.4.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove THF
  3. additionthe crude material was diluted with water
  4. extractionThe mixture was extracted twice with ethyl acetate
  5. washThe collected organic layers were washed with water and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto give the crude product

Sources & evidence

ORD record
ord-bb2bfb33b9174a2eaaaa4ead9e5fad81
Source dataset
uspto-grants-2015_04
Patent number
US09000044B2

Reaction notes

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