Lithium hydroxide, monohydrate → HCID 71711384, compound

HRID 1468420Notes

Reaction equation

HRID 1468420 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:37])[CH2:7][C:8]1[C:17]([CH3:18])=[C:16]([C:19]2[CH:24]=[CH:23][C:22]([S:25](=[O:35])(=[O:34])[NH:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:21][CH:20]=2)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Cl:36])[CH:14]=2)[CH:9]=1.C1COCC1.O>CCCCCC>[CH2:27]([NH:26][S:25]([C:22]1[CH:21]=[CH:20][C:19]([C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([Cl:36])[CH:14]=3)[CH:9]=[C:8]([CH2:7][C:6]([OH:37])=[O:5])[C:17]=2[CH3:18])=[CH:24][CH:23]=1)(=[O:35])=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 21881883Oxolane--water (1/1)HCID 86695011HCID 86695011, compound

Product 1

HCID 71711384HCID 71711384, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Lithium hydroxide monohydrate (0.031 g, 0.70 mmol) was added to a solution of [4-(4-benzylsulfamoyl-phenyl)-6-chloro-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 [4-(4-benzylsulfamoyl-phenyl)-6-chloro-3-methyl-naphthalen-2-yl]-acetic acid (0.080 g, 92%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.38-12.59 (m, 1 H), 8.34 (t, J=6.40 Hz, 1 H), 7.97 (d, J=8.20 Hz, 1 H), 7.88-7.93 (m, 3 H), 7.50 (dd, J=8.60, 2.40 Hz, 1 H), 7.40 (d, J=8.31 Hz, 2 H), 7.17-7.32 (m, 5 H), 7.03 (d, J=1.47 Hz, 1 H), 4.18 (d, J=5.87 Hz, 2 H), 3.86 (s, 2 H), 2.04 (s, 3 H). MS calcd. for C26H21ClNO4S [(M−H)−] 478, obsd. 478.2.

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-77b17bc1e4024795a52f24ac949324ca
Source dataset
uspto-grants-2015_04
Patent number
US09000044B2

Reaction notes

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