Hydrochloric Acid → HCID 22137275, compound

HRID 1827560Notes

Reaction equation

HRID 1827560 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]([O:34][CH2:35][CH2:36][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]=[CH:17][C:16]=1[O:21]C1CCCCO1)(=[O:12])=[O:11].Cl.C(=O)(O)[O-].[Na+]>C(O)C>[OH:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH2:14][N:13]([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][N:37]2[CH2:41][CH2:40][CH2:39][CH2:38]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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 22137421HCID 22137421, compound

Product 1

HCID 22137275HCID 22137275, compoundYield 11.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,4,6-trimethyl-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-N-[2-(tetrahydro-pyran-2-yloxy)-benzyl]-benzenesulfonamide (0.039 g, 0.07 mmol) in 4 mL absolute ethanol was added 1 mL of 1.2N HCl. The reaction mixture was stirred at room temperature for 24 hr. and was poured into saturated aqueous sodium bicarbonate. The aqueous solution was washed with two portions of ethyl acetate. The combined organic layers were dried (sodium sulfate), filtered, and concentrated. The residue was purified by preparative TLC (1.0 mm silica gel layer, eluting with 10% methanol/methylene chloride) to afford 0.004 g of the title compound. MS 494.8 (M+1)+

Workup

  1. washThe aqueous solution was washed with two portions of ethyl acetate
  2. dry with materialThe combined organic layers were dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by preparative TLC (1.0 mm silica gel layer, eluting with 10% methanol/methylene chloride)

Sources & evidence

ORD record
ord-e96a4bf7b8694485a032e3dc881d44c3
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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