Hydrochloric Acid → HCID 58355124, compound

HRID 1509563Notes

Reaction equation

HRID 1509563 reaction equation
[OH:1][CH2:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:6]=[N:5][C:4]=1[C:14]([N:16]([CH2:34][CH:35]([CH3:37])[CH3:36])[C@@H:17]1[CH2:22][N:21]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:20][C@H:19]([C:30]([O:32]C)=[O:31])[CH2:18]1)=[O:15].[Cl-].[NH4+].Cl>C1COCC1.CO.O.[OH-].[Na+]>[C:26]([O:25][C:23]([N:21]1[CH2:22][C@@H:17]([N:16]([C:14]([C:4]2[N:5]=[N:6][N:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:3]=2[CH2:2][OH:1])=[O:15])[CH2:34][CH:35]([CH3:37])[CH3:36])[CH2:18][C@@H:19]([C:30]([OH:32])=[O:31])[CH2:20]1)=[O:24])([CH3:28])([CH3:29])[CH3:27]

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 58355333HCID 58355333, compound

Product 1

HCID 58355124HCID 58355124, compoundYield 99.6%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

1-tert-Butyl 3-methyl (3R,5S)-5-[{[5-(hydroxymethyl)-1-phenyl-1H-1,2,3-triazol-4-yl]carbonyl}(2-methylpropyl)amino]piperidine-1,3-dicarboxylate (2.25 g) was dissolved in THF (10 ml)-methanol (10 ml)-water (8 ml), 8M aqueous sodium hydroxide solution (1.5 ml) was added and the reaction mixture was stirred at room temperature for 3 hr. The reaction mixture was neutralized with saturated aqueous ammonium chloride solution, acidified with 1M hydrochloric acid and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the object product (2.18 g).

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c5f69dcf5545449dba9913900db2108b
Source dataset
uspto-grants-2015_12
Patent number
US09221836B2

Reaction notes

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