Lithium hydroxide, monohydrate → {6-Chloro-3-methyl-4-[4-(piperidine-1-sulfonyl)-phenyl]-naphthalen-2-yl}-acetic acid

HRID 1468415Notes

Reaction equation

HRID 1468415 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:35])[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[CH2:33][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]([Cl:34])[CH:14]=2)[CH:9]=1.C1COCC1.O>CCCCCC>[Cl:34][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH2:7][C:6]([OH:35])=[O:5])[C:17]([CH3:18])=[C:16]2[C:19]1[CH:20]=[CH:21][C:22]([S:25]([N:28]2[CH2:33][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 86695007{6-Chloro-3-methyl-4-[4-(piperidine-1-sulfonyl)-phenyl]-naphthalen-2-yl}-acetic acid methyl ester

Product 1

HCID 71711380{6-Chloro-3-methyl-4-[4-(piperidine-1-sulfonyl)-phenyl]-naphthalen-2-yl}-acetic acidYield 101.1%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Lithium hydroxide monohydrate (0.046 g, 1.1 mmol) was added to a stirred solution of {6-chloro-3-methyl-4-[4-(piperidine-1-sulfonyl)-phenyl]-naphthalen-2-yl}-acetic acid methyl ester (0.130 g, 0.27 mmol) in a 3:1 mixture of THF—H2O mixture (15 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-chloro-3-methyl-4-[4-(piperidine-1-sulfonyl)-phenyl]-naphthalen-2-yl}-acetic acid (0.125 g, 99%) as a solid. 1H NMR (DMSO-d6) δ: 12.51 (br. s, 1H), 7.98 (d, J=8.8 Hz, 1H), 7.88-7.95 (m, 3H), 7.53 (d, J=8.3 Hz, 2H), 7.50 (dd, J=8.8, 1.5 Hz, 1H), 7.01 (s, 1H), 3.87 (s, 2H), 3.02 (t, J=4.9 Hz, 4H), 2.08 (s, 3H), 1.59 (br. s, 4H), 1.33-1.49 (m, 2H). MS calcd. for C24H25ClNO4S [(M+H)+] 458, obsd. 458.4.

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-c4d33ec64ecf42bd8e0e0e471e1e2821
Source dataset
uspto-grants-2015_04
Patent number
US09000044B2

Reaction notes

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