Hydrochloric Acid → HCID 58531349, compound

HRID 1889635Notes

Reaction equation

HRID 1889635 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH2:14][OH:15])[CH:11]=[C:10]([CH2:16][N:17]([CH2:28][C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[S:18]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH:9]=2)=[CH:4][CH:3]=1.CCN(CC)CC.[CH3:43][S:44](Cl)(=[O:46])=[O:45].Cl>CCOC(C)=O>[CH3:43][S:44]([O:15][CH2:14][C:12]1[CH:13]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:9]=[C:10]([CH2:16][N:17]([CH2:28][C:29]2[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=2)[S:18]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH:11]=1)(=[O:46])=[O:45]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58531513HCID 58531513, compound

Product 1

HCID 58531349HCID 58531349, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent3×

Procedure

To a solution of N-((4′-fluoro-5-(hydroxymethyl)biphenyl-3-yl)methyl)-N-(4-fluorobenzyl)-4-methylbenzenesulfonamide (100 mg, 0.203 mmol) and Et3N (0.15 mL) in EtOAc (5 mL) at −30° C. was added methanesulfonyl chloride (25 mg, 0.218 mmol) in EtOAc (10 mL) slowly with stirring. After 1 h, a small amount of 1N aq HCl and EtOAc were added to the reaction mixture. The EtOAc layer was separated, dried over MgSO4 and concentrated in vacuo to obtain the product as a viscous material. It was enough pure to use for next step without any further purification. MS (ESI): (M+H)+=572.18.

Workup

  1. customThe EtOAc layer was separated
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customto obtain the product as a viscous material
  5. customto use for next step without any further purification

Sources & evidence

ORD record
ord-52c62a69c414486792c190780e7b43c2
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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