Sodium Carbonate → 1-(Tert-butoxycarbonylamino)-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinone

HRID 2086223Notes

Reaction equation

HRID 2086223 reaction equation
[C:1]([O:5][C:6]([NH:8][N:9]1[CH2:14][CH2:13][NH:12][CH2:11][C:10]1=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[Cl:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[CH:29]=[C:28]([S:33](Cl)(=[O:35])=[O:34])[CH:27]=[CH:26]2>C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][N:9]1[CH2:14][CH2:13][N:12]([S:33]([C:28]2[CH:27]=[CH:26][C:25]3[C:30](=[CH:31][CH:32]=[C:23]([Cl:22])[CH:24]=3)[CH:29]=2)(=[O:34])=[O:35])[CH2:11][C:10]1=[O:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 106351296-Chloronaphthalene-2-sulfonyl chlorideHCID 227272141-(Tert-butoxycarbonylamino)-2-piperazinone

Product 1

HCID 227270351-(Tert-butoxycarbonylamino)-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The resultant solution of 1-(tert-butoxycarbonylamino)-2-piperazinone in ethyl acetate (20 ml) and a 10% aqueous solution of sodium carbonate (20 ml) was treated at 0° C. with 6-chloronaphthalene-2-sulfonyl chloride (1.36 g) and stirred at room temperature for 30 minutes. The organic phase was separated, washed with brine, dried and concentrated. The residue thus obtained was purified by a column chromatography on a silica gel (hexane:ethyl acetate=1:2) to obtain 1-(tert-butoxycarbonylamino)-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinone (848 mg) as a colorless amorphous solid.

Workup

  1. customThe organic phase was separated
  2. washwashed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue thus obtained
  6. customwas purified by a column chromatography on a silica gel (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-b181143b4c984fae9636cee6c93fb8d0
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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