Triethylamine → HCID 22346254, compound

HRID 897344Notes

Reaction equation

HRID 897344 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][NH2:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.Cl[CH2:20][CH2:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[CH:21]([S:22]([NH:11][CH2:10][CH2:9][NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])(=[O:24])=[O:23])=[CH2:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 187201N-BOC-ethylenediamine

Product 1

HCID 22346254HCID 22346254, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-Boc ethylenediamine (1.24 g, 7.74 mmol) in methylene chloride (35 ml) at −10 C, was added triethylamine (2.37 ml, 17.0 mmol). 2-chloro-1-ethanesulfonyl chloride (0.809 mL, 7.74 mmol). After 4 hr at −10 C the cold bath was removed and the reaction was stirred for 12 hr at room temperature. The reaction was quenched by the addition of Na2CO3 (sat aq.) and extracted with methylene chloride. The organic extracts were dried (MgSO4) and the solvent evaporated in vacuo to afford the title compound as an oil which was used in the next step without further purification.

Workup

  1. customAfter 4 hr at −10 C the cold bath was removed
  2. customThe reaction was quenched by the addition of Na2CO3 (sat aq.)
  3. extractionextracted with methylene chloride
  4. dry with materialThe organic extracts were dried (MgSO4)
  5. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-7bb4ef92b8f94de4b303ffaf9be7c9d7
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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