Benzoyl chloride → HCID 178519538, compound

HRID 853135Notes

Reaction equation

HRID 853135 reaction equation
[CH:1]1([CH2:4][NH:5][C@H:6]2[CH2:11][CH2:10][C@H:9]([C:12]([O:21][Si](CC)(CC)CC)([C:17]([F:20])([F:19])[F:18])[C:13]([F:16])([F:15])[F:14])[CH2:8][CH2:7]2)[CH2:3][CH2:2]1.CCN(CC)CC.[C:36](Cl)(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[NH4+].[Cl-]>CCOCC.ClCCCl.C1COCC1>[CH:1]1([CH2:4][N:5]([C@H:6]2[CH2:11][CH2:10][C@H:9]([C:12]([OH:21])([C:13]([F:15])([F:14])[F:16])[C:17]([F:20])([F:19])[F:18])[CH2:8][CH2:7]2)[C:36](=[O:43])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:2][CH2:3]1

Participants

8

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 178477570HCID 178477570, compound

Product 1

HCID 178519538HCID 178519538, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 50 mg (0.12 mmol) of trans cyclopropylmethyl-[4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-cyclohexyl]-amine in 3 mL of a 1:2-mixture of THF and 1,2-dichloroethane was treated with 0.03 mL (0.23 mmol) of NEt3 and 0.02 mL (0.14 mmol) of benzoylchloride. The mixture was stirred at RT for 2 hrs and distributed between a saturated aqueous solution of NH4Cl and Et2O. After drying of the combined organic phases over Na2SO4 and evaporation of the solvent the residue was redissolved in 2 mL of THF, treated with an excess of TBAF and distributed between a saturated aqueous solution of NH4Cl and Et2O. Drying of the combined organic phases over Na2SO4 and column chromatography on silica gel with heptane/EtOAc 2:1 gave 35 mg (72%) of trans N-cyclopropylmethyl-N-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-cyclohexyl]-benzamide as a white solid, MS: 424, (M+H)+.

Workup

  1. dry with materialAfter drying of the combined organic phases over Na2SO4 and evaporation of the solvent the residue
  2. dissolutionwas redissolved in 2 mL of THF
  3. additiontreated with an excess of TBAF
  4. dry with materialDrying of the combined organic phases over Na2SO4 and column chromatography on silica gel with heptane/EtOAc 2:1

Sources & evidence

ORD record
ord-1aa90c8974534cd1a9bf4f80e69f25f4
Source dataset
uspto-grants-2007_08
Patent number
US07253282B2

Reaction notes

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