Lithium hydroxide, monohydrate → HCID 71711574, compound

HRID 1468442Notes

Reaction equation

HRID 1468442 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:42])[CH2:7][C:8]1[C:17]([CH3:18])=[C:16]([C:19]2[CH:24]=[CH:23][C:22]([S:25](=[O:40])(=[O:39])[N:26]([CH:36]([CH3:38])[CH3:37])[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]([F:41])[CH:14]=2)[CH:9]=1.C1COCC1.O>CCCCCC>[F:41][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH2:7][C:6]([OH:42])=[O:5])[C:17]([CH3:18])=[C:16]2[C:19]1[CH:20]=[CH:21][C:22]([S:25](=[O:39])(=[O:40])[N:26]([CH:36]([CH3:38])[CH3:37])[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 86695024HCID 86695024, compound

Product 1

HCID 71711574HCID 71711574, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Lithium hydroxide monohydrate (0.051 g, 1.23 mmol) was added to a solution of (6-fluoro-4-{4-[isopropyl-(4-methoxy-benzyl)-sulfamoyl]-phenyl}-3-methyl-naphthalen-2-yl)-acetic acid methyl ester (0.17 g, 0.30 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 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-fluoro-4-{4-[isopropyl-(4-methoxy-benzyl)-sulfamoyl]-phenyl}-3-methyl-naphthalen-2-yl)-acetic acid (0.138 g, 82%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.49 (br. s, 1 H), 7.98-8.04 (m, 3 H), 7.90-7.92 (m, 1 H), 7.47 (d, J=7.80 Hz, 1 H), 7.39 (td, J=8.60, 2.40 Hz, 1 H), 7.33 (d, J=8.00 Hz, 2 H), 6.91 (d, J=8.20 Hz, 2 H), 6.67 (dd, J=11.00, 2.60 Hz, 1 H), 4.41-4.44 (m, 2 H), 4.13 (spt, J=6.80 Hz, 1 H), 3.86 (s, 2H), 3.74 (s, 3H), 2.08 (s, 3H), 0.93 (d, J=6.85 Hz, 6 H). MS calcd. for C30H29FNO5S [(M−H)−] 534, obsd. 534.3.

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-7f189b6f9dae4acd8ec8828d7dda49ff
Source dataset
uspto-grants-2015_04
Patent number
US09000044B2

Reaction notes

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