Triethylamine → HCID 15550574, compound

HRID 2268285Notes

Reaction equation

HRID 2268285 reaction equation
[C:1]([O:5][C:6](=[O:10])[CH:7](N)[CH3:8])([CH3:4])([CH3:3])[CH3:2].C([N:13](CC)CC)C.[CH2:18]([O:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1)[C:19]#[C:20][CH3:21]>ClCCl>[CH2:18]([O:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH:13][CH2:8][CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:10])(=[O:31])=[O:30])=[CH:25][CH:24]=1)[C:19]#[C:20][CH3:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4351123Tert-butyl 2-aminopropanoateHCID 111959284-But-2-ynyloxy-benzenesulfonyl chloride

Product 1

HCID 15550574HCID 15550574, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To tert-butyl-2-aminopropanoate (2.0 g, 11.0 mmol) in 20 mL of dichloromethane at 0° C. was added triethylamine (6.75 mL, 48.4 mmol) followed by 4-(2-butynyloxy)phenylsulfonyl chloride (2.94 g, 12.1 mmol). An additional 10 mL of dichloromethane was added to the thick slurry. The mixture was stirred overnight then diluted with dichloromethane and washed sequentially with water, 2N aqueous citric acid and brine, then dried over anhydrous sodium sulfate. Filtration and concentration in vacuo gave a solid that was triturated with hexanelethyl acetate to give tert-butyl 3-({[4-(2-butynyloxy)phenyl]sulfonyl}amino)propanoate (3.88 g) as an off-white solid, mp 63-65° C. Analysis for C17H23NO5S: Calc'd: C, 57.77; H, 6.56; N, 3.96. Found: C, 57.68; H, 6.42; N, 3.90. Electrospray Mass Spec 354.2 (M+H)+.

Workup

  1. washwashed sequentially with water, 2N aqueous citric acid and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationFiltration and concentration in vacuo
  4. customgave a solid
  5. customthat was triturated with hexanelethyl acetate

Sources & evidence

ORD record
ord-eb1237435d6e4836967d722bceda197b
Source dataset
uspto-grants-2001_12
Patent number
US06326516B1

Reaction notes

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