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Triethylamine → HCID 66868579, compound

HRID 68612
Notes
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Reaction equation

HRID 68612 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:22]=[C:21]([CH2:23][NH:24][CH3:25])[CH:20]=[CH:19][C:9]=2[O:10][CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:4][C:3]=1[S:26]([CH3:29])(=[O:28])=[O:27].CCN(CC)CC.[F:37][C:38]1[CH:43]=[CH:42][C:41]([S:44](Cl)(=[O:46])=[O:45])=[CH:40][CH:39]=1>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:22]=[C:21]([CH2:23][N:24]([CH3:25])[S:44]([C:41]3[CH:42]=[CH:43][C:38]([F:37])=[CH:39][CH:40]=3)(=[O:46])=[O:45])[CH:20]=[CH:19][C:9]=2[O:10][CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:4][C:3]=1[S:26]([CH3:29])(=[O:27])=[O:28]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 67528897t-Butyl 2-(2-(4-fluoro-3-(methylsulfonyl)phenyl)-4-((methylamino)methyl)phenoxy)acetate

Product 1

HCID 66868579HCID 66868579, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent
2×

Conditions

Temperature
0 °C

Procedure

To secondary amine 30 (150 mg, 0.35 mmol, 1 eq.) in dry DCM (15 mL) at 0° C. was added Et3N (3 mL) followed by dropwise addition of a DCM solution of 4-fluorobenzenesulfonyl chloride (90 mg, 0.42 mmol, 1.2 eq). After stirring at 0° C. for 20 min, the mixture was stirred at room temperature for 2 h. The reaction was extracted between DCM and water and the organic layer was washed with 1N HCl, saturated NaHCO3 solution, and brine, dried (Na2SO4), and concentrated in vacuo to give 150 mg (72%) of t-butyl 2-((4-fluoro-3-(methylsulfonyl)phenyl)-4-((4-fluoro-N-methylphenylsulfonamido)methyl)phenoxy)acetate (31) as oil which was used in the next step without further purification.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 h
  2. extractionThe reaction was extracted between DCM and water
  3. washthe organic layer was washed with 1N HCl, saturated NaHCO3 solution, and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6217006d55254ab6952b54688f3fabdd
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822467B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes