Triethylamine → (R)-2-(4-Fluoro-3,5-dimethyl-phenylamino)-6-(3-nitro-benzenesulfonylamino)-hexanoic acid methyl ester

HRID 885507Notes

Reaction equation

HRID 885507 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C@H:4]([NH:10][C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([F:18])=[C:13]([CH3:19])[CH:12]=1)[CH2:5][CH2:6][CH2:7][CH2:8][NH2:9].[N+:21]([C:24]1[CH:25]=[C:26]([S:30](Cl)(=[O:32])=[O:31])[CH:27]=[CH:28][CH:29]=1)([O-:23])=[O:22].C(N(CC)CC)C>ClCCl>[CH3:1][O:2][C:3](=[O:20])[C@H:4]([NH:10][C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([F:18])=[C:13]([CH3:19])[CH:12]=1)[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][S:30]([C:26]1[CH:27]=[CH:28][CH:29]=[C:24]([N+:21]([O-:23])=[O:22])[CH:25]=1)(=[O:31])=[O:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 84763-Nitrobenzenesulfonyl chlorideHCID 69169741(R)-6-Amino-2-(4-fluoro-3,5-dimethyl-phenylamino)-hexanoic acid methyl ester

Product 1

HCID 69169788(R)-2-(4-Fluoro-3,5-dimethyl-phenylamino)-6-(3-nitro-benzenesulfonylamino)-hexanoic acid methyl esterYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-6-amino-2-(4-fluoro-3,5-dimethyl-phenylamino)-hexanoic acid methyl ester (0.200 g, 0.709 mmol) and 3-nitro-benzenesulfonyl chloride (0.157 g, 0.709 mmol) in 10 mL of dichloromethane, was added triethylamine (0.5 mL, 3.544 mmol). After stirring at room temperature under N2 for 16 h, the reaction mixture was concentrated under reduced pressure. The product was isolated by Flash chromatography (silica gel) eluting with 20-50% ethyl acetate/hexanes to give the title compound as light yellow semi-solid (0.128 g, 39% yield). LC-MS: tR=9.5 min; m/z 468 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe product was isolated by Flash chromatography (silica gel)
  3. washeluting with 20-50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-7cf43ab67f7b41228c6e263f8fc4d602
Source dataset
uspto-grants-2012_08
Patent number
US08242174B2

Reaction notes

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