Ethyl bromoacetate → HCID 69654994, compound

HRID 1061354Notes

Reaction equation

HRID 1061354 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]3)=[CH:17][CH:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:33]([O:32][C:30](=[O:31])[CH2:29][N:14]([S:11]([C:8]1[CH:7]=[CH:6][C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[CH:10][CH:9]=1)(=[O:13])=[O:12])[C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:22][CH2:23][C:24](=[O:27])[CH2:25][CH2:26]2)=[CH:17][CH:16]=1)[CH3:34]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 22220211HCID 22220211, compound

Product 1

HCID 69654994HCID 69654994, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 0.12 g of 4-butyl-N-[4-(4-oxo-piperidine-1-yl)-phenyl]-benzenesulfonamide (which was obtained in Example 247), 0.038 mL of ethyl bromoacetate and 0.047 g of potassium carbonate in 10 mL acetonitrile was refluxed overnight. The solvent was removed in vacuo and the residue was purified by flash chromatography (8:1 Hexanes: EtOAc-1:1 Hexanes: EtOAc) to give 0.107 g of the title compound as a yellow gum; 1H NMR (300 MHz, CDCl3) δ 0.93 (t, J=7.26 Hz, 3H), 1.19-1.26 (m, 3H), 1.31-1.43 (m, 2H), 1.57-1.66 (m, 2H), 2.52 (t, J=6.03 Hz, 4H), 2.67 (t, J-7.56 Hz, 2H), 3.60 (t, J=6.00 Hz, 4H), 4.14 (q, J=7.14 Hz, 2H), 4.35 (s, 2H), 6.80-6.85 (m, 2H), 7.06-7.12 (m, 2H), 7.24 (m, 2H), 7.59 (d, J=8.28 Hz, 2H); MS (ES) m/z: 473.0 (MH+); HRMS found for C25H32N2O5S: 472.2028.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by flash chromatography (8:1 Hexanes: EtOAc-1:1 Hexanes: EtOAc)

Sources & evidence

ORD record
ord-002be3aadeca43b79da4dfaeb3933440
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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