Hydrochloric Acid → HCID 23579139, compound

HRID 1827593Notes

Reaction equation

HRID 1827593 reaction equation
[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][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.O1CCCC1.O1CCOCC1>[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][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 23157422HCID 23157422, compound

Product 1

HCID 23579139HCID 23579139, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-{4-[[3-(tetrahydro-pyran-2-yloxy)-benzyl]-(2,4,6-trimethyl-benzenesulfonyl)-amino]-phenyl}-propionic acid methyl ester in 0.5 mL methanol and 0.3 mL tetrahydrofuran was added HCl (0.52 mL of a 4.0M solution in 1,4-dioxane, 2.09 mmol) and triethylsilane (0.134 mL, 0.84 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. Preparative thin layer chromatography afforded 0.059 g of 3-{4-[(3-hydroxy-benzyl)-(2,4,6-trimethyl-benzenesulfonyl)-amino]-phenyl}-propionic acid methyl ester. 1H NMR (CDCl3) δ 7.03 (t, 1H, J=8.0 Hz), 6.95–6.80 (m, 6H), 6.68–6.62 (m, 2H), 6.48 (bs, 1H), 4.69 (s, 2H), 3.59 (s, 3H), 2.81 (t, 2H, J=7.6 Hz), 2.51 (t, 2H, J=7.6 Hz), 2.41 (s, 6H), 2.24 (s, 3H).

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-e60c75d419f84081ac6875875b9ded3d
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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