Triethylamine → HCID 15896077, compound

HRID 366469Notes

Reaction equation

HRID 366469 reaction equation
C(N(CC)CC)C.[CH2:8]([O:10][C:11](=[O:21])[CH2:12][NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:9].[S:22](Cl)([Cl:25])(=[O:24])=[O:23]>C(Cl)Cl>[CH2:14]([N:13]([S:22]([Cl:25])(=[O:24])=[O:23])[CH2:12][C:11]([O:10][CH2:8][CH3:9])=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24648Sulfuryl chlorideHCID 80908N-Benzylglycine ethyl ester

Product 1

HCID 15896077HCID 15896077, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of triethylamine (2.0 ml, 14.4 mmol) and N-benzylglycine ethyl ester (2.25 ml, 12.0 mmol) in methylene chloride (5 ml) was added to a solution of sulfuryl chloride (0.96 ml, 12.0 mmol) in methylene chloride (30 ml) at -78° C. The reaction mixture was stirred at -78° C. for 4 h and then concentrated. Ether (75 ml) was added and the resulting precipitate was filtered. The organic layer was washed with 1M HCl and brine, dried over MgSO4 and concentrated in vacuo to give ethyl 2-[benzyl-(chlorosulfonyl)amino]acetate as a colorless oil (69%).

Workup

  1. concentrationconcentrated
  2. additionEther (75 ml) was added
  3. filtrationthe resulting precipitate was filtered
  4. washThe organic layer was washed with 1M HCl and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-824ddb11b3114b32906d7fda79934585
Source dataset
uspto-grants-2000_10
Patent number
US06130220

Reaction notes

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