Hydrochloric Acid → HCID 68283164, compound

HRID 1527516Notes

Reaction equation

HRID 1527516 reaction equation
C1(S([CH:10]([F:27])/[C:11](=[N:19]\S(C(C)(C)C)(=O)=O)/[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Br:18])[CH:13]=2)(=O)=O)C=CC=CC=1.OP([O-])([O-])=O.[Na+].[Na+].[ClH:35].O1CCOCC1>CO>[ClH:35].[Br:18][C:14]1[CH:13]=[C:12]([C@H:11]([NH2:19])[CH2:10][F:27])[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24203Sodium Phosphate, DibasicHCID 312751,4-DioxaneHCID 141630695(NZ)-N-[2-(benzenesulfonyl)-1-(3-bromophenyl)-2-fluoroethylidene]-2-methylpropane-2-sulfonamide

Product 1

HCID 68283164HCID 68283164, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-20 °C

Procedure

To a mixture of 2-methyl-propane-2-sulfonic acid [2-benzenesulfonyl-1-(3-bromo-phenyl)-2-fluoro-eth-(Z)-ylidene]-amide (1.74 g, 3.76 mmol) and sodium phosphate dibasic (4.27 g, 30.1 mmol) in methanol (50 mL), cooled to −20° C., was added Na/Hg amalgam (6.92 g, 30.1 mmol). The reaction mixture was stirred for 1 h at −20° C., followed by filtration. To the filtrate was added a 4N HCl solution in dioxane (9.41 mL, 37.6 mmol), followed by stirring for 30 min at 25° C. After evaporation of volatiles, Et2O was added to the residue and the resulting precipitate was filtered off. The title compound thus obtained was used in the next reaction step without further purification. MS (LC/MS): 218/220 [M+H]+; tR (HPLC conditions f): 1.05 min.

Workup

  1. filtrationfollowed by filtration
  2. stirringby stirring for 30 min at 25° C
  3. customAfter evaporation of volatiles, Et2O
  4. additionwas added to the residue
  5. filtrationthe resulting precipitate was filtered off

Sources & evidence

ORD record
ord-d717e1609e054765a3823ef846a5376b
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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