Hydrochloric Acid → HCID 69591918, compound

HRID 1827584Notes

Reaction equation

HRID 1827584 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:10]([N:13]([C:28]1[CH:33]=[CH:32][C:31]([CH:34]=[CH:35][C:36](=[O:42])[N:37]2[CH2:41][CH2:40][CH2:39][CH2:38]2)=[CH:30][CH:29]=1)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21]C2CCCCO2)[CH:16]=1)(=[O:12])=[O:11].Cl.[SiH](CC)(CC)CC.C(=O)(O)[O-].[Na+]>CO.O1CCOCC1>[OH:21][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=1)[CH2:14][N:13]([C:28]1[CH:33]=[CH:32][C:31]([CH:34]=[CH:35][C:36](=[O:42])[N:37]2[CH2:38][CH2:39][CH2:40][CH2:41]2)=[CH:30][CH:29]=1)[S:10]([C:3]1[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[CH3:1])(=[O:12])=[O:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 69591907HCID 69591907, compound

Product 1

HCID 69591918HCID 69591918, compoundYield 68.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2,4,6-trimethyl-N-[4-(3-oxo-3-pyrrolidin-1-yl-propenyl)-phenyl]-N-[3-(tetrahydro-pyran-2-yloxy)-benzyl]-benzenesulfonamide (0.021 g, 34.9 μmol) in 0.5 mL methanol was added HCl (0.19 mL of a 4.0 M solution in 1,4-dioxane, 2 mmol) and Et3SiH (0.047 ml, 0.30 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 dried (magnesium sulfate) and concentrated. The residue was purified by preparative TLC (eluting with 10% methanol/methylene chloride) to afford 0.012 g of N-(3-hydroxybenzyl)-2,4,6-trimethyl-N-[4-(3-oxo-3-pyrrolidin-1-yl-propenyl)-phenyl]-benzenesulfonamide. 1H NMR (acetone-d6) δ 6.16 (d, 1H, J=15.6 Hz), 6.02–5.98 (m, 2H), 5.71–5.67 (m, 3H), 5.57 (s, 2H), 5.35–5.26 (m, 4H), 3.43 (s, 2H), 2.29–2.19 (m, 4H), 1.13 (s, 6H), 0.95 (s, 3H), 0.72–0.56 (m, 4H).

Workup

  1. washthe aqueous solution was washed with methylene chloride
  2. dry with materialThe organic layer was dried (magnesium sulfate)
  3. concentrationconcentrated
  4. customThe residue was purified by preparative TLC (eluting with 10% methanol/methylene chloride)

Sources & evidence

ORD record
ord-0758fcd0e5e24b718fc9337e530f04e0
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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