Triethylamine → tert-butyl 3-chloro-5-((3,5-dichloro-2-hydroxy-N-isobutylphenylsulfonamido)methyl)benzyl(isobutyl)carbamate

HRID 1889640Notes

Reaction equation

HRID 1889640 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([CH2:21][NH:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH:20]=1)[CH2:5][N:6]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].CCN(CC)CC.[Cl:34][C:35]1[C:36]([OH:46])=[C:37]([S:42](Cl)(=[O:44])=[O:43])[CH:38]=[C:39]([Cl:41])[CH:40]=1>C(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([CH2:21][N:22]([CH2:23][CH:24]([CH3:26])[CH3:25])[S:42]([C:37]2[CH:38]=[C:39]([Cl:41])[CH:40]=[C:35]([Cl:34])[C:36]=2[OH:46])(=[O:43])=[O:44])[CH:20]=1)[CH2:5][N:6]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 900783,5-Dichloro-2-hydroxybenzenesulphonyl chlorideHCID 66616572Tert-butyl 3-chloro-5-((isobutylamino)methyl)benzyl(isobutyl)carbamate

Product 1

HCID 58531453tert-butyl 3-chloro-5-((3,5-dichloro-2-hydroxy-N-isobutylphenylsulfonamido)methyl)benzyl(isobutyl)carbamateYield 73.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 3-chloro-5-((isobutylamino)methyl)benzyl(isobutyl)carbamate (2.4 g, 6.27 mmol) in CH2Cl2 (30 mL) was added Et3N (1.3 mL, 9.40 mmol), followed by the addition of 3,5-dichloro-2-hydroxybenzenesulfonyl chloride (1.80 g, 6.89 mmol). The reaction mixture was stirred at rt for 2 h. The mixture was diluted with CH2Cl2 and water. The organic layer was washed with saturated NaHCO3 solution, NH4Cl solution, brine solution, and dried over MgSO4. The filtrate was concentrated and the residue was purified by silica gel flash chromatography. The column was eluted with hexane to 80% dichloromethane in hexane. The fractions containing the desired product were combined and concentrated to give colorless viscous solid (2.8 g, 72%).

Workup

  1. washThe organic layer was washed with saturated NaHCO3 solution, NH4Cl solution, brine solution
  2. dry with materialdried over MgSO4
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by silica gel flash chromatography
  5. washThe column was eluted with hexane to 80% dichloromethane in hexane
  6. additionThe fractions containing the desired product
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8d8afe46468d4085b42d54342236d66c
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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