Hydrochloric Acid → HCID 58171490, compound

HRID 1752326Notes

Reaction equation

HRID 1752326 reaction equation
[CH3:1][N:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]([CH:14]3[CH2:18][CH2:17][N:16]([C:19]([O:21][CH:22]4[CH:29]5[CH2:30][C:25]6([C:32]([O:34]C)=[O:33])[CH2:26][CH:27]([CH2:31][CH:23]4[CH2:24]6)[CH2:28]5)=[O:20])[CH2:15]3)=[N:12][CH:13]=2)=[CH:4][C:3]1=[O:36].O.[Li+].[OH-].Cl>CO>[CH3:1][N:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]([CH:14]3[CH2:18][CH2:17][N:16]([C:19]([O:21][CH:22]4[CH:23]5[CH2:24][C:25]6([C:32]([OH:34])=[O:33])[CH2:26][CH:27]([CH2:28][CH:29]4[CH2:30]6)[CH2:31]5)=[O:20])[CH2:15]3)=[N:12][CH:13]=2)=[CH:4][C:3]1=[O:36]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 58171510HCID 58171510, compound

Product 1

HCID 58171490HCID 58171490, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(methoxycarbonyl)adamantan-4-yl 3-(5-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)pyrimidin-2-yl)pyrrolidine-1-carboxylate (36 mg, 0.073 mmol) in MeOH (6 mL)/water (2 mL) was added LiOH (22 mg, 0.73 mmol). The reaction mixture was heated to reflux for 1 h. The formed mixture was concentrated to give an oil which was adjusted pH=5 by 0.5 M HCl and extracted with EtOAc (10 mL×3). The combined organic layers were dried over sodium sulfate, filtered and concentrated to afford 4-((3-(5-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)pyrimidin-2-yl)pyrrolidine-1-carbonyl)oxy)adamantane-1-carboxylic acid (20 mg, 55%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 h
  3. concentrationThe formed mixture was concentrated
  4. customto give an oil which
  5. extractionextracted with EtOAc (10 mL×3)
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-89db0b9c5a944184ae1a2db5fba7bfef
Source dataset
uspto-grants-2015_10
Patent number
US09163012B2

Reaction notes

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