Triethylamine → HCID 57798321, compound

HRID 2100317Notes

Reaction equation

HRID 2100317 reaction equation
[CH2:1]([S:4](Cl)(=[O:6])=[O:5])[CH2:2][CH3:3].[N:8]1([C:14]2([CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:17][NH:16][CH2:15]2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.C(N(CC)CC)C.CN(C)CCN>ClCCl>[N:8]1([C:14]2([CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])[CH2:17][N:16]([S:4]([CH2:1][CH2:2][CH3:3])(=[O:6])=[O:5])[CH2:15]2)[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 66053N,N-DimethylethylenediamineHCID 662791-Propanesulfonyl chlorideHCID 57798317HCID 57798317, compound

Product 1

HCID 57798321HCID 57798321, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Propane-1-sulfonyl chloride (0.44 ml, 3.9 mmol) was added to tert-butyl [(3-morpholin-4-ylazetidin-3-yl)methyl]carbamate (0.71 g, 2.6 mmol) and triethylamine (0.91 g, 6.5 mmol) in dichloromethane (9 ml) at 0° C. The reaction was then stirred at room temperature for 30 mins before quenching with N,N-dimethylethylenediamine (0.5 eq). The resulting mixture was partitioned between dichloromethane and water. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and evaporated to dryness to give crude tert-butyl {[3-morpholin-4-yl-1-(propylsulfonyl)azetidin-3-yl]methyl}carbamate which was used without further purification m/z (M++H) 378.

Workup

  1. customThe resulting mixture was partitioned between dichloromethane and water
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-02569a0775b7493788368ae632421285
Source dataset
uspto-grants-2009_08
Patent number
US07572792B2

Reaction notes

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