HCID 22672861, compound → HCID 22672855, compound

HRID 1006718Notes

Reaction equation

HRID 1006718 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[C:21]([CH3:22])=[CH:20][C:19]([N+:23]([O-])=O)=[CH:18][C:17]=2[CH3:26])=[CH:11][C:10]=1[S:27]([NH:30][CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])(=[O:29])=[O:28])C1C=CC=CC=1>[Pd].C1COCC1>[NH2:23][C:19]1[CH:20]=[C:21]([CH3:22])[C:16]([O:15][C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([S:27]([NH:30][CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])(=[O:29])=[O:28])[CH:11]=2)=[C:17]([CH3:26])[CH:18]=1

Participants

4

Reactant 1

HCID 22672861HCID 22672861, compound

Product 1

HCID 22672855HCID 22672855, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the title F compound, 2-benzyloxy-5-(2,6-dimethyl-4-nitrophenoxy)-N-(2,2-dimethylpropyl)benzenesulfonamide (1.22 g, 2.45 mmol) and palladium on activated carbon (10 wt. %; 250 mg) in 40 mL of THF is stirred under hydrogen atmosphere (H2, 1 atm) for 8 h. The catalyst is removed by vacuum filtration through celite, washed with THF and the combined filtrate and washings are concentrated. The residue is suspended in CH2Cl2 and the product is collected by vacuum filtration, washed with CH2Cl2 and dried to give 5-(4-amino-2,6-dimethyl-phenoxy)-2-hydroxy-N-(2,2-dimethylpropyl)benzenesulfonamide: NMR (DMSO-d6) 0.80 (s, 9H), 1.90 (s, 6H), 2.55 (d, 2H, J=7.5), 4.90 (br s, 2H), 6.31 (s, 2H), 6.87 (br s, 1H), 6.93 (br s, 2H), 6.97 (t, 1H, J=7.5), 10.13 (s, 1H).

Workup

  1. customThe catalyst is removed by vacuum filtration through celite
  2. washwashed with THF
  3. concentrationthe combined filtrate and washings are concentrated
  4. filtrationthe product is collected by vacuum filtration
  5. washwashed with CH2Cl2
  6. customdried

Sources & evidence

ORD record
ord-f1f0952c52e34a5990651b3458708fc0
Source dataset
uspto-grants-2004_09
Patent number
US06790978B2

Reaction notes

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