Benzoic Acid → HCID 69783397, compound

HRID 1765544Notes

Reaction equation

HRID 1765544 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:30]=[CH:29][C:28]([CH2:31][C@@H:32]([OH:36])[CH2:33][NH:34][CH3:35])=[CH:27][C:12]=1[C:13]([NH:15][CH2:16][C:17]12[CH2:26][CH:21]3[CH2:22][CH:23]([CH2:25][CH:19]([CH2:20]3)[CH2:18]1)[CH2:24]2)=[O:14].COC(C)(C)C>CC(O)C>[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:30]=[CH:29][C:28]([CH2:31][C@@H:32]([OH:36])[CH2:33][NH:34][CH3:35])=[CH:27][C:12]=1[C:13]([NH:15][CH2:16][C:17]12[CH2:24][CH:23]3[CH2:22][CH:21]([CH2:20][CH:19]([CH2:25]3)[CH2:18]1)[CH2:26]2)=[O:14]

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 15413tert-Butyl methyl etherHCID 21107392HCID 21107392, compound

Product 1

HCID 69783397HCID 69783397, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Benzoic acid (11.07 g) was added to a suspension of 2-chloro-5-[(2R)-2-hydroxy-3-(methylamino)propyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamide (Example 15c)) (33.54 g, 86 mmol) in 2-propanol (333 mL) and the mixture heated to reflux whereupon a clear solution was obtained. t-Butyl methyl ether (1 L) was added dropwise over 30 minutes and the solution maintained at reflux. The solution was allowed to cool to room temperature, stirred for a further 2 hours and solid collected by filtration, washed with t-butyl methyl ether and dried in vacuo at 40° C. to give the titled compound (24.5 g). The mother liquors were evaporated in vacuo and the residue dissolved in 2-propanol (50 mL) at reflux, t-butyl methyl ether (150 mL) was added and a second crop was isolated as before to give further titled compound (13 g).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux whereupon a clear solution
  3. customwas obtained
  4. temperaturethe solution maintained
  5. temperatureat reflux
  6. filtrationsolid collected by filtration
  7. washwashed with t-butyl methyl ether
  8. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-72b4c0d1a23e4b599ee0d6ac4ffdfbd8
Source dataset
uspto-grants-2007_06
Patent number
US07227038B2

Reaction notes

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