Triethylamine → HCID 93038209, compound

HRID 1861631Notes

Reaction equation

HRID 1861631 reaction equation
[NH2:1][C@H:2]([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].Cl.C(N(CC)CC)C.[CH2:19]([S:21](Cl)(=[O:23])=[O:22])[CH3:20]>ClCCl>[CH2:19]([S:21]([NH:1][C@H:2]([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5])(=[O:23])=[O:22])[CH3:20]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 11667Ethanesulfonyl chlorideHCID 2723695Leucine methyl ester hydrochloride

Product 1

HCID 93038209HCID 93038209, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of 3.0 g of H-Leu-OMe.HCl in 30 mL of dichloromethane was adjusted to pH 8 using triethylamine and cooled at 0° C. Then 3.2 mL of ethanesulfonyl chloride and 2.3 mL of triethylamine were added. After stirring for 16 h at room temperature the reaction mixture was washed successively with 0.5 N hydrochloric acid, water and aqueous 5% sodium hydrogencarbonate and concentrated. The crude product was purified by chromatography on silica gel (eluent: dichloromethane/methanol=9/1 v/v) to yield 3.3 g of EtSO2-Leu-OMe.

Workup

  1. washwas washed successively with 0.5 N hydrochloric acid, water and aqueous 5% sodium hydrogencarbonate
  2. concentrationconcentrated
  3. customThe crude product was purified by chromatography on silica gel (eluent: dichloromethane/methanol=9/1 v/v)

Sources & evidence

ORD record
ord-c10b6d89c7534e47b53145e78c18737a
Source dataset
uspto-grants-2003_03
Patent number
US06534495B1

Reaction notes

Loading…