4-Chlorobenzenesulfonyl chloride → HCID 8349071, compound

HRID 2242336Notes

Reaction equation

HRID 2242336 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[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:2][O:3][C:4](=[O:11])[C@H:5]([C@H:7]([CH2:9][CH3:10])[CH3:8])[NH:6][S:19]([C:16]1[CH:17]=[CH:18][C:13]([Cl:12])=[CH:14][CH:15]=1)(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 11171351Isoleucine methyl ester hydrochloride

Product 1

HCID 8349071HCID 8349071, compoundYield 110.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of L-isoleucine methyl ester hydrochloride (1.82 g, 10 mmol) and 4-chlorobenzenesulfonyl chloride (2.11 g, 10 mmol) in CH2Cl2 was added triethylamine (4.18 mL, 30 mmol). The mixture was stirred at 25° C. for 16 hours, then filtered and concentrated. The crude product was purified by flash chromatography over silica gel using 10% ethyl acetate in hexane to give N-4-chlorobenzenesulfonyl L-isoleucine methyl ester 3.53 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-9f88cfee9d1b4c49982e7a24dc3be2a8
Source dataset
uspto-grants-2010_03
Patent number
US07671075B2

Reaction notes

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