Sodium Carbonate → 1-[1-(tert-Butoxycarbonyl)-4-piperidinylamino]-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinone

HRID 2086233Notes

Reaction equation

HRID 2086233 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][N:15]2[CH2:20][CH2:19][NH:18][CH2:17][C:16]2=[O:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[Cl:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[CH:35]=[C:34]([S:39](Cl)(=[O:41])=[O:40])[CH:33]=[CH:32]2>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([NH:14][N:15]2[CH2:20][CH2:19][N:18]([S:39]([C:34]3[CH:33]=[CH:32][C:31]4[C:36](=[CH:37][CH:38]=[C:29]([Cl:28])[CH:30]=4)[CH:35]=3)(=[O:40])=[O:41])[CH2:17][C:16]2=[O:21])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 106351296-Chloronaphthalene-2-sulfonyl chlorideHCID 695459311-[1-(Tert-butoxycarbonyl)-4-piperidinylamino]-2-piperazinone

Product 1

HCID 695456311-[1-(tert-Butoxycarbonyl)-4-piperidinylamino]-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of the resultant 1-[1-(tert-butoxycarbonyl)-4-piperidinylamino]-2-piperazinone in ethyl acetate (30 ml) and a 10% aqueous solution of sodium carbonate (30 ml) was combined at 0° C. with 6-chloronaphthalene-2-sulfonyl chloride (2.24 g) and stirred at room temperature for 30 minutes, and then 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-[1-(tert-Butoxycarbonyl)-4-piperidinylamino]-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinone (3.55 g) as a colorless amorphous material.

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-8f99910822204a77a931c07b751824dc
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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