Hydrochloric Acid → HCID 69591931, compound

HRID 1827590Notes

Reaction equation

HRID 1827590 reaction equation
[CH3:1][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]C3CCCCO3)[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.Cl.C([SiH](CC)CC)C.C(=O)(O)[O-].[Na+]>CO.C(Cl)Cl.O1CCOCC1>[CH3:1][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]([OH:32])[CH:27]=2)[S:13]([C:16]2[C:17]([CH3:24])=[CH:18][C:19]([CH3:23])=[CH:20][C:21]=2[CH3:22])(=[O:15])=[O:14])=[CH:8][CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 69591801HCID 69591801, compound

Product 1

HCID 69591931HCID 69591931, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-{4-[[3-(tetrahydro-pyran-2-yloxy)-benzyl]-(2,4,6-trimethylbenzenesulfonyl)-amino]-phenyl}-acrylic acid methyl ester in 0.5 mL MeOH and 0.2 mL methylene chloride was added HCl (0.78 mL of a 4.0M solution in 1,4-dioxane, 3.12 mmol) and triethylsilane (0.20 mL, 1.25 mmol). The reaction mixture was stirred at room temperature for 24 hr. Saturated aqueous sodium bicarbonate was added and the aqueous solution was washed with methylene chloride. The organic layer was separated, dried (magnesium sulfate), and concentrated. Medium pressure silica gel chromatography (methylene chloride to 5% ethyl acetate/methylene chloride) afforded 0.050 g of 3-{4-[(3-hydroxy-benzyl)-(2,4,6-trimethyl-benzenesulfonyl)-amino]-phenyl}-acrylic acid methyl ester. MS 466.4 (M+1)+

Workup

  1. washthe aqueous solution was washed with methylene chloride
  2. customThe organic layer was separated
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7083c5dde9f2401ea82ff7c798d5ebff
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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