Hydrochloric Acid → HCID 57892103, compound

HRID 1820872Notes

Reaction equation

HRID 1820872 reaction equation
[C:1]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:6]=[CH:5][C:4]([C:7](=[O:30])[CH2:8][C:9]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([O:22][CH2:23][CH2:24][N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[C:16]([CH:21]=2)[C:17]([O:19]C)=[O:18])=[O:10])=[CH:3][CH:2]=1.[OH-].[Na+].Cl>CO>[C:1]1([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:2]=[CH:3][C:4]([C:7](=[O:30])[CH2:8][C:9]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([O:22][CH2:23][CH2:24][N:25]3[CH2:26][CH2:27][CH2:28][CH2:29]3)=[C:16]([CH:21]=2)[C:17]([OH:19])=[O:18])=[O:10])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 11225514HCID 11225514, compound2×

Product 1

HCID 57892103HCID 57892103, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

0.25 g (0.51 mmol) of methyl 5-(3-biphenyl-4-yl-3-oxopropionylamino)-2-(2-pyrrolidin-1-ylethoxy)benzoate (compound 1.9) is dissolved in 20 mL of methanol, 2.0 mL of 1N sodium hydroxide solution is added, and the mixture is stirred for 3 hours at 50° C. and 12 hours at ambient temperature. After this time, another 1.0 mL of 1N sodium hydroxide solution is added and the mixture is stirred for another 3 hours at 50° C. After cooling, 3.0 mL of 1N hydrochloric acid is added and the mixture is stirred for 1 hour at ambient temperature. The solvent is evaporated down, and the residue is taken up in a little methanol and the precipitate obtained is suction filtered and dried in vacuo at 80° C. Yield: 240 mg (100% of theory); Rf value: 0.20 (silica gel, methylene chloride/methanol/ammonia=9:1:0.1); m.p. 236° C.-240° C.; C28H28N2O5; EII mass spectrum: m/z=473 [M+H]+.

Workup

  1. stirringthe mixture is stirred for another 3 hours at 50° C
  2. temperatureAfter cooling
  3. stirringthe mixture is stirred for 1 hour at ambient temperature
  4. customThe solvent is evaporated down
  5. customthe precipitate obtained
  6. filtrationfiltered
  7. customdried in vacuo at 80° C

Sources & evidence

ORD record
ord-33e66d77e32d4044802605777c16744e
Source dataset
uspto-grants-2009_10
Patent number
US07605176B2

Reaction notes

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