Triethylamine → 1-tert-Butylcarbamoyl-4-(4-but-2-ynyloxy-benzenesulfonylmethyl)-piperidine-4-carboxylic acid ethyl ester

HRID 278339Notes

Reaction equation

HRID 278339 reaction equation
[C:1]([N:5]=[C:6]=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:8]([O:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH2:22][C:23]2([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)(=[O:21])=[O:20])=[CH:15][CH:14]=1)[C:9]#[C:10][CH3:11].C(N(CC)CC)C>C(Cl)Cl>[CH2:32]([O:31][C:29]([C:23]1([CH2:22][S:19]([C:16]2[CH:15]=[CH:14][C:13]([O:12][CH2:8][C:9]#[C:10][CH3:11])=[CH:18][CH:17]=2)(=[O:21])=[O:20])[CH2:24][CH2:25][N:26]([C:6](=[O:7])[NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:27][CH2:28]1)=[O:30])[CH3:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62412tert-Butyl isocyanateHCID 22626999HCID 22626999, compound

Product 1

HCID 538812481-tert-Butylcarbamoyl-4-(4-but-2-ynyloxy-benzenesulfonylmethyl)-piperidine-4-carboxylic acid ethyl esterYield 73.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butylisocyanate (0.097 ml, 0.85 mmol) in 8.0 mL of CH2Cl2, was added 4-[[[4-(2-Butynyloxy)phenyl]sulfonyl]methyl]-4-piperidinecarboxylic acid ethyl ester (prepared from example 36, step 2) (0.337 g, 0.81 mmol) and triethylamine (0.135 ml, 0.97 mmol) and stirred at room temperature for 2 h. The reaction was diluted with CH2Cl2 and washed with H2O, brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was triturated with ether:hexanes (1:1) to provide 0.284 g (73%) of the desired product as a white solid. Electrospray Mass Spec: 479.2 (M+H)+

Workup

  1. washwashed with H2O, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with ether:hexanes (1:1)

Sources & evidence

ORD record
ord-63f9f5137e5544c7a574fff2ed17ab77
Source dataset
uspto-grants-2002_03
Patent number
US06358980B1

Reaction notes

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