Hydrochloric Acid → HCID 58531394, compound

HRID 1889648Notes

Reaction equation

HRID 1889648 reaction equation
[Cl:1][C:2]1[C:3]([OH:38])=[C:4]([S:9]([N:12]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[CH2:13][C:14]2[CH:19]=[C:18]([CH2:20][OH:21])[CH:17]=[C:16]([O:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[CH:15]=2)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH3:39][S:40](Cl)(=[O:42])=[O:41].CCN(CC)CC.Cl>CCOC(C)=O>[CH3:39][S:40]([O:21][CH2:20][C:18]1[CH:17]=[C:16]([O:22][C:23]2[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=2)[CH:15]=[C:14]([CH2:13][N:12]([CH2:30][C:31]2[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=2)[S:9]([C:4]2[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[C:3]=2[OH:38])(=[O:11])=[O:10])[CH:19]=1)(=[O:42])=[O:41]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 58531487HCID 58531487, compound

Product 1

HCID 58531394HCID 58531394, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 3,5-dichloro-N-(4-fluorobenzyl)-N-(3-(4-fluorophenoxy)-5-(hydroxymethyl)benzyl)-2-hydroxybenzenesulfonamide (1.1 g, 1.895 mmol) and methanesulfonyl chloride (0.147 mL, 1.895 mmol) in EtOAc at −30° C. was added Et3N (0.4 mL, 2.87 mmol) under Ar atm. The mixture was stirred for 1 h, but only a small amount of product was produced. Thus, additional methanesulfonyl chloride (0.25 mL) and Et3N (0.6 mL) were added at −30° C. The mixture was slowly warmed to rt, stirred at rt for 2 h and treated with 1N aq HCl and EtOAc. The EtOAc layer was separated, washed with water, dried over MgSO4 and concentrated in vacuo to obtain the desired product as a viscous material (˜1.4 g). This material was used directly for the next step without further purification. 1H NMR (CDCl3): δ 7.61 (d, J=2.8 Hz, 1H), 7.57 (d, J=2.2 Hz, 1H), 7.07-6.89 (m, 8H), 6.82 (d, J=1.6 Hz, 2H), 6.63 (s, 1H), 5.06 (s, 2H), 4.37 (s, 2H), 4.34 (s, 2H), 2.97 (s, 3H; MS: (M−H)−=656.1.

Workup

  1. customonly a small amount of product was produced
  2. stirringstirred at rt for 2 h
  3. customThe EtOAc layer was separated
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8d3a092a73a34c03bdfb4749eded08e9
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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