Diisopropylethylamine → tert-Butyl 4-((3,5-dichloro-N-(4-fluorobenzyl)-2-hydroxyphenylsulfonamido)methyl)benzylcarbamate

HRID 1889665Notes

Reaction equation

HRID 1889665 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][CH2:8][C:9]2[CH:23]=[CH:22][C:12]([CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[Cl:26][C:27]1[C:28]([OH:38])=[C:29]([S:34](Cl)(=[O:36])=[O:35])[CH:30]=[C:31]([Cl:33])[CH:32]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[Cl:26][C:27]1[C:28]([OH:38])=[C:29]([S:34]([N:7]([CH2:8][C:9]2[CH:23]=[CH:22][C:12]([CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[CH:11][CH:10]=2)[CH2:6][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:25][CH:24]=2)(=[O:36])=[O:35])[CH:30]=[C:31]([Cl:33])[CH:32]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 900783,5-Dichloro-2-hydroxybenzenesulphonyl chlorideHCID 66616762tert-Butyl 4-((4-fluorobenzylamino)methyl)benzylcarbamate

Product 1

HCID 66616495tert-Butyl 4-((3,5-dichloro-N-(4-fluorobenzyl)-2-hydroxyphenylsulfonamido)methyl)benzylcarbamateYield 212.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 4-((4-fluorobenzylamino)methyl)benzylcarbamate (654 mg, 1.90 mmol, Aldrich) in CH2Cl2 (5 mL) were added 3,5-dichloro-2-hydroxybenzene-1-sulfonyl chloride (497 mg, 0.50 mmol, Aldrich) and diisopropylethylamine (1.34 mL, 9.50 mmol). The reaction mixture was stirred at rt overnight. The mixture was diluted with methylene chloride (100 mL) and washed with saturated aq sodium bicarbonate solution and brine, dried over MgSO4, concentrated and purified by flash column chromatography on silica gel eluting with CH2Cl2/EtOAc to give the title compound (604 mg, 53%) as a white solid. MS (ESI): m/z 566.9.

Workup

  1. washwashed with saturated aq sodium bicarbonate solution and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. custompurified by flash column chromatography on silica gel eluting with CH2Cl2/EtOAc

Sources & evidence

ORD record
ord-4c634a531dc84bb18a13373080622b22
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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