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

HRID 1468422Notes

Reaction equation

HRID 1468422 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:39])[CH2:7][C:8]1[C:17]([CH3:18])=[C:16]([C:19]2[CH:24]=[CH:23][C:22]([S:25](=[O:37])(=[O:36])[NH:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)=[CH:21][CH:20]=2)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Cl:38])[CH:14]=2)[CH:9]=1.C1COCC1.O>CCCCCC>[Cl:38][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH2:7][C:6]([OH:39])=[O:5])[C:17]([CH3:18])=[C:16]2[C:19]1[CH:20]=[CH:21][C:22]([S:25](=[O:36])(=[O:37])[NH:26][CH2:27][C:28]2[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=2)=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 21881883Oxolane--water (1/1)HCID 86695012{6-Chloro-4-[4-(4-methoxy-benzylsulfamoyl)-phenyl]-3-methyl-naphthalen-2-yl}-acetic acid methyl ester

Product 1

HCID 71711447{6-Chloro-4-[4-(4-methoxy-benzylsulfamoyl)-phenyl]-3-methyl-naphthalen-2-yl}-acetic acidYield 98%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Lithium hydroxide monohydrate (0.029 g, 0.68 mmol) was added to a solution {6-chloro-4-[4-(4-methoxy-benzylsulfamoyl)-phenyl]-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (0.090 g, 0.18 mmol) in a 3:1 mixture of THF—H2O mixture (12 mL). The reaction mixture was stirred for 16 hours at room temperature. The reaction mixture was concentrated to remove the 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 gave {6-chloro-4-[4-(4-methoxy-benzylsulfamoyl)-phenyl]-3-methyl-naphthalen-2-yl}-acetic acid (0.086 g, 98%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.43-12.61 (m, 1 H), 8.22 (t, J=6.30 Hz, 1 H), 7.98 (d, J=8.80 Hz, 1 H), 7.89-7.95 (m, 3 H), 7.49 (dd, J=8.80, 2.20 Hz, 1 H), 7.42 (d, J=7.83 Hz, 2 H), 7.15 (d, J=8.80 Hz, 2 H), 7.04 (d, J=1.96 Hz, 1 H), 6.81-6.86 (m, 2 H), 4.09 (d, J=5.87 Hz, 2 H), 3.86 (s, 2 H), 3.68 (s, 3 H), 2.06 (s, 3 H). MS calcd. for C27H23ClNO5S [(M−H)−] 508, obsd. 508.3.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove the 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-64a7e8909efd499784321d7d40356932
Source dataset
uspto-grants-2015_04
Patent number
US09000044B2

Reaction notes

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