Toluene → HCID 86749461, compound

HRID 1721651Notes

Reaction equation

HRID 1721651 reaction equation
[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[C:4]([O:12][CH:13]([CH3:17])[C:14]#[C:15][CH3:16])[CH:3]=1.[C:18](Cl)(=[O:25])[O:19][CH2:20][C:21]([Cl:24])([Cl:23])[Cl:22].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>ClCCl>[Cl:11][C:10]1[C:2]([NH:1][C:18]([O:19][CH2:20][C:21]([Cl:24])([Cl:23])[Cl:22])=[O:25])=[CH:3][C:4]([O:12][CH:13]([CH3:17])[C:14]#[C:15][CH3:16])=[C:5]([CH:9]=1)[C:6]([NH2:8])=[O:7]

Participants

6

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 870632,2,2-Trichloroethyl chloroformateHCID 19694201HCID 19694201, compound

Product 1

HCID 86749461HCID 86749461, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.75 g of (S)-N-(8-methyl-8-azabicyclo 3.2.1!oct-3α-yl)-4-amino-5-chloro-2-(1-methyl-2-butynyl)oxybenzamide, 0.51 g of 2,2,2-trichloroethyl chlorocarbonate and 0.41 g of potassium carbonate were added to toluene. The obtained mixture was refluxed for 3 hours and cooled, followed by the addition thereto of dichloromethane. The resulting mixture was washed with 1N hydrochloric acid, dried over magnesium sulfate, and freed from the solvent. The residue was purified by silica gel column chromatography (ethyl acetate/n-hexane (1:4) mixture) to give 0.50 g of (S)-N-(8-(2,2,2-trichloroethoxycarbonyl)-8-azabicyclo 3.2.1!oct-3α-yl)-5-chloro-2-(1-methyl-2-butynyl)oxy-4-(2,2,2-trichloroethoxycarbonylamino)benzamide.

Workup

  1. temperatureThe obtained mixture was refluxed for 3 hours
  2. temperaturecooled
  3. additionfollowed by the addition
  4. washThe resulting mixture was washed with 1N hydrochloric acid
  5. dry with materialdried over magnesium sulfate
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/n-hexane (1:4) mixture)

Sources & evidence

ORD record
ord-a2504512c88042efba762a98e6c070c1
Source dataset
uspto-grants-1996_04
Patent number
US05512579

Reaction notes

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