4-Chloro-2-hydroxybenzaldehyde → 1-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-4-(7-chloro-2H-benzopyran-3-sulfonyl)-2-piperazinone

HRID 2186154Notes

Reaction equation

HRID 2186154 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]2[CH2:20][CH2:19][N:18]([S:21]([CH:24]=[CH2:25])(=[O:23])=[O:22])[CH2:17][C:16]2=[O:26])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:27][C:28]1[CH:29]=[C:30]([OH:36])[C:31](=[CH:34][CH:35]=1)[CH:32]=O.CC(C)([O-])C.[K+]>C(O)(C)(C)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]2[CH2:20][CH2:19][N:18]([S:21]([C:24]3[CH2:25][O:36][C:30]4[CH:29]=[C:28]([Cl:27])[CH:35]=[CH:34][C:31]=4[CH:32]=3)(=[O:22])=[O:23])[CH2:17][C:16]2=[O:26])[CH2:10][CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 5201014-Chloro-2-hydroxybenzaldehydeHCID 234474501-[1-(Tert-butoxycarbonyl)piperidin-4-ylmethyl]-4-vinylsulfonyl-2-piperazinoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 234473471-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-4-(7-chloro-2H-benzopyran-3-sulfonyl)-2-piperazinoneYield 34.3%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of the obtained 1-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-4-vinylsulfonyl-2-piperazinone (3.99 g) and 4-chlorosalicylaldehyde (1.61 g) in tert-butanol (35 ml) was added potassium t-butoxide (446 mg), and the mixture was refluxed for 4 days. The reaction solution was concentrated, and the residue was partitioned with ethyl acetate/water. The organic layer was washed with brine, dried and concentrated, and the residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:4) to give colorless solid of 1-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-4-(7-chloro-2H-benzopyran-3-sulfonyl)-2-piperazinone (1.856 g).

Workup

  1. temperaturethe mixture was refluxed for 4 days
  2. concentrationThe reaction solution was concentrated
  3. customthe residue was partitioned with ethyl acetate/water
  4. washThe organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customthe residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:4)

Sources & evidence

ORD record
ord-34b755bff8d3433382fbc2e8a087aa27
Source dataset
uspto-grants-2002_06
Patent number
US06403595B1

Reaction notes

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