Benzenepropanoyl chloride → HCID 86602509, compound

HRID 1822137Notes

Reaction equation

HRID 1822137 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([O:17][Si](CC)(CC)CC)([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[NH:25][CH2:26][CH3:27].CCN(C(C)C)C(C)C.[C:37]1([CH2:43][CH2:44][C:45](Cl)=[O:46])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C(Cl)Cl.C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([OH:17])([C:9]([F:11])([F:12])[F:10])[C:13]([F:14])([F:15])[F:16])[CH:5]=[CH:4][C:3]=1[N:25]([CH2:26][CH3:27])[C:45](=[O:46])[CH2:44][CH2:43][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

7

Reactant 4

HCID 64801Benzenepropanoyl chlorideHCID 81531DiisopropylethylamineHCID 2724141Tetrabutylammonium FluorideHCID 86602507HCID 86602507, compound

Product 1

HCID 86602509HCID 86602509, compoundYield 67.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 100 mg (0.23 mmol) of [2-chloro-4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-phenyl]-N-ethyl-amine in CH2Cl2 was treated with 0.08 mL (0.46 mmol) of DIPEA and 0.07 mL (0.46 mmol) of 3-phenylpropionylchloride. The mixture was stirred at RT for 10 hours and treated with 0.4 mL of a 1 M TBAF-solution in THF. Evaporation of the solvent and column chromatography on silica gel with n-heptane/EtOAc 4:1 yielded 70 mg (67%) of N-[2-chloro-4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenyl]-N-ethyl-3-phenyl-propionamide, light yellow oil, MS: 454 (MH+, 1Cl).

Workup

  1. customEvaporation of the solvent and column chromatography on silica gel with n-heptane/EtOAc 4:1

Sources & evidence

ORD record
ord-d079ba4cc0224fe3b280703edb170bc6
Source dataset
uspto-grants-2009_10
Patent number
US07608721B2

Reaction notes

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