Hydrochloric Acid → HCID 69591877, compound

HRID 1827580Notes

Reaction equation

HRID 1827580 reaction equation
C[O:2][C:3](=[O:39])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][O:34]3)[CH:27]=2)[S:13]([C:16]2[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=2[CH3:24])(=[O:15])=[O:14])=[CH:8][CH:7]=1.[OH-].[Na+].Cl.C(OCC)(=O)C>O1CCCC1.O>[O:34]1[CH2:35][CH2:36][CH2:37][CH2:38][CH:33]1[O:32][C:28]1[CH:27]=[C:26]([CH:31]=[CH:30][CH:29]=1)[CH2:25][N:12]([S:13]([C:16]1[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=1[CH3:24])(=[O:15])=[O:14])[C:9]1[CH:8]=[CH:7][C:6]([CH:5]=[CH:4][C:3]([OH:39])=[O:2])=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 69591801HCID 69591801, compound

Product 1

HCID 69591877HCID 69591877, compoundYield 98.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-{4-[[3-(tetrahydro-pyran-2-yloxy)-benzyl]-(2,4,6-trimethyl-benzenesulfonyl)-amino]-phenyl}-acrylic acid methyl ester (1.83 g, 3.33 mmol) in 4 mL tetrahydrofuran was added sodium hydroxide (0.399 g, 9.98 mmol) in 3 mL water. The reaction mixture was stirred at room temperature overnight. The reaction mixture was adjusted to a pH of 4 with 1 N HCl and ethyl acetate and water were added. The layers were separated and the organic layer was washed with two portions of water and then with saturated aqueous sodium chloride. The combined aqueous layers were back-extracted with ethyl acetate. The combined organic layers were dried (magnesium sulfate) and concentrated to afford 1.756 g (98%) of the title compound. MS 534.3 (M−1)−

Workup

  1. additionwere added
  2. customThe layers were separated
  3. washthe organic layer was washed with two portions of water
  4. extractionThe combined aqueous layers were back-extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried (magnesium sulfate)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-52170f56f93a43c58995c4b504df1e75
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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