Triethylamine → 5-Chlorothiophene-2-sulfonyl isoleucine methyl ester

HRID 640040Notes

Reaction equation

HRID 640040 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:11])[C@H:5]([C@H:7]([CH2:9][CH3:10])[CH3:8])[NH2:6].[Cl:12][C:13]1[S:17][C:16]([S:18](Cl)(=[O:20])=[O:19])=[CH:15][CH:14]=1.C(N(CC)CC)C>>[CH3:2][O:3][C:4](=[O:11])[C@H:5]([C@H:7]([CH2:9][CH3:10])[CH3:8])[NH:6][S:18]([C:16]1[S:17][C:13]([Cl:12])=[CH:14][CH:15]=1)(=[O:20])=[O:19]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 27339255-Chlorothiophene-2-sulfonyl chlorideHCID 11171351Isoleucine methyl ester hydrochloride

Product 1

HCID 213561115-Chlorothiophene-2-sulfonyl isoleucine methyl esterYield 77.6%

Conditions

Temperature
60 °C

Procedure

To a solution of L-isoleucine methyl ester hydrochloride (1.82 g, 10 mmol) and 5-chlorothiophene-2-sulfonyl chloride (1.82 g, 10 mmol) was added triethylamine (4.18 mL, 30 mmol). The mixture was stirred at 60° C. overnight, then filtered and concentrated. The crude product was purified by flash chromatography over silica gel using 10% ethyl acetate in hexane to give 5-chlorothiophene-2-sulfonyl isoleucine methyl ester 2.53 g.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe crude product was purified by flash chromatography over silica gel using 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-c6d6522c7e5f47b089ae135b3613d506
Source dataset
uspto-grants-2010_04
Patent number
US07691884B2

Reaction notes

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