Hydrochloric Acid → HCID 10239323, compound

HRID 1373855Notes

Reaction equation

HRID 1373855 reaction equation
O1CCCC1.[OH-].[Na+].[CH:8]1([C:14]2[CH:45]=[CH:44][C:17]([CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]4[N:27]=[C:28]([N:31]([CH2:33][C:34]5[CH:43]=[CH:42][C:37]([C:38]([O:40]C)=[O:39])=[CH:36][CH:35]=5)[CH3:32])[S:29][CH:30]=4)=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.Cl>O.CO>[CH:8]1([C:14]2[CH:45]=[CH:44][C:17]([CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]4[N:27]=[C:28]([N:31]([CH2:33][C:34]5[CH:35]=[CH:36][C:37]([C:38]([OH:40])=[O:39])=[CH:42][CH:43]=5)[CH3:32])[S:29][CH:30]=4)=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 23023934HCID 23023934, compound

Product 1

HCID 10239323HCID 10239323, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Tetrahydrofuran (250 ml), methanol (250 ml) and a 2N-aqueous sodium hydroxide solution (95.0 ml, 190 mmol) were added to methyl 4-(N-(4-(4-(4-cyclohexylbenzyloxy)phenyl)-2-thiazolyl)-N-methylaminomethyl)benzoate (50.0 g, 94.9 mmol) obtained in Example 2(4), and the mixture was heated under reflux for 40 min under an argon atmosphere. Water (310 ml) was added to the reaction mixture and the mixture was cooled to room temperature. 2N-Hydrochloric acid (95.0 ml, 190 mmol) was added dropwise and the mixture was stirred for 90 min. The resulting crystals were collected by filtration, washed with water (700 mL) and dried to give the title compound (48.5 g, yield 99.7%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 40 min under an argon atmosphere
  3. filtrationThe resulting crystals were collected by filtration
  4. washwashed with water (700 mL)
  5. customdried

Sources & evidence

ORD record
ord-4bc92efff09944549318d0c44a96248f
Source dataset
uspto-grants-2007_01
Patent number
US07163952B2

Reaction notes

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