Triethylamine → HCID 57959395, compound

HRID 2091449Notes

Reaction equation

HRID 2091449 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].C(N(CC)CC)C.[C:19]([C:21]1[CH:22]=[C:23]([S:27](Cl)(=[O:29])=[O:28])[CH:24]=[CH:25][CH:26]=1)#[N:20]>O1CCOCC1>[C:19]([C:21]1[CH:22]=[C:23]([S:27]([NH:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:10])[CH3:9])(=[O:29])=[O:28])[CH:24]=[CH:25][CH:26]=1)#[N:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 187201N-BOC-ethylenediamineHCID 28013603-Cyanobenzene-1-sulfonyl chloride2×

Product 1

HCID 57959395HCID 57959395, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirring mixture consisting of tert-butyl 2-aminoethylcarbamate (Sigma-Aldrich, 832 mg), triethylamine (1.44 mL), and 1,4-dioxane (25 mL) was added 3-cyanobenzene-1-sulfonyl chloride (Compound 14, Sigma-Aldrich, 942 mg) and the mixture was stirred overnight. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and 5% aqueous potassium hydrogen sulfate. The organic phase was washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford the title intermediate (1.52 g), which was carried on without further purification.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and 5% aqueous potassium hydrogen sulfate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3316988d925743739b186838c62536c7
Source dataset
uspto-grants-2013_05
Patent number
US08440417B2

Reaction notes

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