Water → n-Benzo[b]thiophene-2-ylcarbonyl-l-leucine methyl ester

HRID 413232Notes

Reaction equation

HRID 413232 reaction equation
[S:1]1[C:5]([C:6](Cl)=[O:7])=[CH:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.[CH3:13][O:14][C:15](=[O:22])[C@H:16]([CH2:18][CH:19]([CH3:21])[CH3:20])[NH2:17].C(N(C(C)C)CC)(C)C.O>C(Cl)Cl>[CH3:13][O:14][C:15](=[O:22])[C@H:16]([CH2:18][CH:19]([CH3:21])[CH3:20])[NH:17][C:6]([C:5]1[S:1][C:2]2[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=2[CH:4]=1)=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 65105(+)-L-Leucine methyl esterHCID 81531DiisopropylethylamineHCID 142384Benzo[b]thiophene-2-carbonyl Chloride

Product 1

HCID 32044690n-Benzo[b]thiophene-2-ylcarbonyl-l-leucine methyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzo[b]thiophene-2-carbonyl chloride (4.9 g, 25 mmol) was added to a stirred solution of L-leucine methyl ester (4.5 g, 25 mmol) and diisopropylethylamine (9 ml, 51 mmol) in DCM (200 ml). After stirring for 2 hours at room temperature, the mixture was poured into water and washed with brine and dried (MgSO4). Evaporation under reduced pressure afforded the title compound as a white solid, 7.6 g, 100% yield.

Workup

  1. washwashed with brine
  2. dry with materialdried (MgSO4)
  3. customEvaporation under reduced pressure

Sources & evidence

ORD record
ord-db4ef2c344f14593bcfe27b7bffee420
Source dataset
uspto-grants-2003_05
Patent number
US06566373B2

Reaction notes

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