Dichloromethane → 4-(4-But-2-ynyloxy-benzenesulfonylmethyl)-piperidine-1,4-dicarboxylic acid ethyl ester methyl ester

HRID 353559Notes

Reaction equation

HRID 353559 reaction equation
C([O:3][C:4]([C:6]1([CH2:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]#[C:25][CH3:26])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])C.[CH3:27]/[C:28](/[O:34][Si](C)(C)C)=N\[Si](C)(C)C.[CH3:39][O:40]C(Cl)=O.[CH2:44](Cl)Cl>>[CH3:44][O:3][C:4]([C:6]1([CH2:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]#[C:25][CH3:26])=[CH:18][CH:17]=2)(=[O:14])=[O:15])[CH2:11][CH2:10][N:9]([C:39]([O:34][CH2:28][CH3:27])=[O:40])[CH2:8][CH2:7]1)=[O:5]

Participants

5

Reactant 4

HCID 6344Dichloromethane3×HCID 6586Methyl chloroformateHCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 22626999HCID 22626999, compound

Product 1

HCID 538996104-(4-But-2-ynyloxy-benzenesulfonylmethyl)-piperidine-1,4-dicarboxylic acid ethyl ester methyl esterYield 85%

Conditions

Temperature
0 °C

Procedure

To a solution of 4-[[[4-(2-Butynyloxy)phenyl]sulfonyl]methyl]-4-piperidinecarboxylic acid ethyl ester (0.354 g, 0.85 mmol) in 1.0 mL of CH2Cl2 under N2 atmosphere was added dropwise a solution of N,O-bis(trimethylsilyl)acetamide (0.462 ml, 1.87 mmol) in 0.5 mL of CH2Cl2 and stirred for 1 h The reaction was cooled to 0° C. and added dropwise a solution of 0.079 mL (1.02 mmol) of methylchloroformate in 0.5 mL of CH2Cl2. The reaction was allowed to stir at room temperature for 1 hand cooled to 0° C., quenched with pH 7 buffer solution and extracted with EtOAc. The organics was washed with H2O, brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with EtOAc:hexanes (1:2) to provide 0.315 g (85%) of the desired product as a colorless oil. Electrospray Mass Spec: 438.3 (M+H)+.

Workup

  1. stirringto stir at room temperature for 1 hand
  2. temperaturecooled to 0° C.
  3. customquenched with pH 7 buffer solution
  4. extractionextracted with EtOAc
  5. washThe organics was washed with H2O, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was chromatographed on silica gel eluting with EtOAc:hexanes (1:2)

Sources & evidence

ORD record
ord-a6523a690d084aaea0ad23a8d01b5050
Source dataset
uspto-grants-2004_06
Patent number
US06753337B2

Reaction notes

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