Triethylamine → HCID 20773301, compound

HRID 1814800Notes

Reaction equation

HRID 1814800 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12][C@H:13]1[CH2:18][NH:17][C@H:16]([CH3:19])[CH2:15][N:14]1[C:20](=[O:28])[C@:21]([OH:27])([CH3:26])[C:22]([F:25])([F:24])[F:23].C(N(CC)CC)C>CCOC(C)=O>[CH3:12][C@H:13]1[CH2:18][N:17]([S:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[C@H:16]([CH3:19])[CH2:15][N:14]1[C:20](=[O:28])[C@:21]([OH:27])([CH3:26])[C:22]([F:25])([F:23])[F:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 10587022HCID 10587022, compound

Product 1

HCID 20773301HCID 20773301, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 4-fluorobenzene sulphonyl chloride (234 mg, 1.2 mmol) in EtOAc (10 ml) was added to a stirred mixture of (R)-[(2S,5R)-2-methyl-5-methyl-1-(3,3,3-trifluoro-2-hydroxy-2-methylpropionyl)piperazine] (J. Med. Chem., 1999, 42, 2741-2746) (254 mg, 1.0 mmol) and triethylamine (0.17 ml, 1.2 mmol) in EtOAc (15 ml). The resultant mixture was stirred at ambient temperature for 2 hours, washed with 1 M hydrochloric acid, saturated sodium hydrogen carbonate solution and brine, dried and evaporated. The residue was recrystallized from EtOAc/hexane to give the title compound as a solid (230 mg, 0.56 mmol). Mp: 174-175° C.; NMR: 0.95 (d, 3H), 1.25 (d, 3H), 1.75 (s, 3H), 3.25 (dd, 1H), 3.35 (d, 1H), 3.5 (dd, 1H), 4.15 (m, 2H), 4.3 (s, 1H), 4.75 (s, 1H), 7.2 (d, 2H), 7.8 (d, 2H); m/z 411.

Workup

  1. washwashed with 1 M hydrochloric acid, saturated sodium hydrogen carbonate solution and brine
  2. customdried
  3. customevaporated
  4. customThe residue was recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-91b5fc31cfb641fa9a004afaffde6dcb
Source dataset
uspto-grants-2005_04
Patent number
US06878712B1

Reaction notes

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