Hydrochloric Acid → HCID 58355124, compound

HRID 2169043Notes

Reaction equation

HRID 2169043 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-69bf1de3ea404866a39354d4989ffb74
Source dataset
uspto-grants-2015_06
Patent number
US09045436B2

Reaction notes

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