Acetic Anhydride → 1-[2-(N-formyl-N-hydroxyamino)-2-phenylethanesulfonyl]-4-(4-fluorophenyl)piperazine

HRID 1582048Notes

Reaction equation

HRID 1582048 reaction equation
[OH:1][NH:2][CH:3]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:4][S:5]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)(=[O:7])=[O:6].[C:27](OC(=O)C)(=[O:29])C>C1COCC1.C(O)=O>[CH:27]([N:2]([CH:3]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:4][S:5]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)(=[O:6])=[O:7])[OH:1])=[O:29]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 111764211-[2-(Hydroxyamino)-2-phenylethanesulfonyl]-4-(4-fluorophenyl)piperazine

Product 1

HCID 99312211-[2-(N-formyl-N-hydroxyamino)-2-phenylethanesulfonyl]-4-(4-fluorophenyl)piperazineYield 61%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[2-(hydroxyamino)-2-phenylethanesulfonyl]-4-(4-fluorophenyl)piperazine (338 mg, 0.89 mmol) in THF (5 ml) and formic acid (2 ml) was added a preformed mixture of formic acid (2 ml) and acetic anhydride (0.5 ml). The mixture was stirred at room temperature for one hour. The mixture was evaporated in vacuo and toluene (2×5 ml) was added and evaporated in vacuo. The residue was taken in CH2Cl2-methanol (6 ml, 9:1) and silica (1 g) was added. The mixture was stirred for 18 hours. The silica was filtered off and rinsed with CH2Cl2-methanol (9:1). The residue was purified on silica gel (eluant:CH2Cl2—MeOH 4%) to give the title compound as a light orange solid (220 mg, 61%).

Workup

  1. customThe mixture was evaporated in vacuo and toluene (2×5 ml)
  2. additionwas added
  3. customevaporated in vacuo
  4. additionsilica (1 g) was added
  5. stirringThe mixture was stirred for 18 hours
  6. filtrationThe silica was filtered off
  7. washrinsed with CH2Cl2-methanol (9:1)
  8. customThe residue was purified on silica gel (eluant:CH2Cl2—MeOH 4%)

Sources & evidence

ORD record
ord-6a4acace07604fa2b7605d871c35902e
Source dataset
uspto-grants-2004_05
Patent number
US06734184B1

Reaction notes

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