Lithium hydroxide, monohydrate → HCID 69656586, compound

HRID 7029Notes

Reaction equation

HRID 7029 reaction equation
O.[OH-].[Li+].C[O:5][C:6]([C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]1[NH:14][S:15]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)(=[O:17])=[O:16])=[O:7]>C1COCC1.CO.O>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([S:15]([NH:14][C@H:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C@H:8]2[C:6]([OH:7])=[O:5])(=[O:16])=[O:17])=[CH:19][CH:20]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 69656016HCID 69656016, compound

Product 1

HCID 69656586HCID 69656586, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (1.7 mmol) was added to a mixture of (1R,2S)-2-(4-chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid methyl ester in THF (8 mL), methanol (8mL) and water (8 mL). Reaction stirred at room temperature overnight. Organic solvents were removed from the mixture in vacuo. Remaining aqueous was washed with ether (2×15 mL). Aqueous layer was made acidic to litmus paper with 1 N hydrochloric acid. Mixture was extracted with ethyl acetate (2×20 mL). Combined extracts were washed with brine (1×10 mL) then dried (magnesium sulfate), filtered and concentrated in vacuo. The product (208 mg) was obtained as a white solid in 80% yield: 1H NMR (300 Mz, CDCl3) δ 7.70 (d, 2 H, J=8.8), 7.48 (d, 4 H, J=8.8), 6.20 (d, 1 H, J=9.5), 3.41 (m, 1 H), 2.81 (dd, 1 H, Jd=4.4, Jd=4.8), 2.03 (m, 1 H), 1.80 (m, 1 H), 1.62 (m, 1 H), 1.44 (m, 2 H), 1.25 (m, 2 H); MS m/e 316 (M−H)−.

Workup

  1. customReaction
  2. customOrganic solvents were removed from the mixture in vacuo
  3. washRemaining aqueous was washed with ether (2×15 mL)
  4. extractionMixture was extracted with ethyl acetate (2×20 mL)
  5. washCombined extracts were washed with brine (1×10 mL)
  6. dry with materialthen dried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-92fc3ebc156c49bb94c274736e08c176
Source dataset
uspto-grants-2006_08
Patent number
US07084178B2

Reaction notes

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