Hydroxide → HCID 58355545, compound

HRID 1184278Notes

Reaction equation

HRID 1184278 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@@H:12]([N:14]([C:19]([C:21]2[N:22]=[N:23][N:24]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:25]=2[CH2:26][CH2:27][CH2:28][CH2:29][O:30][CH3:31])=O)[CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:11][C@@H:10](C(O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P([N:55]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[Na].[OH-:59]>C1(C)C=CC=CC=1.C(=O)([O-])O.[Na+].C(N(CC)CC)C>[NH2:55][C@@H:10]1[CH2:11][C@H:12]([N:14]([C:19]([C:21]2[N:22]=[N:23][N:24]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:25]=2[CH2:26][CH2:27][CH2:28][CH2:29][O:30][CH3:31])=[O:59])[CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]1

Participants

8

Reactant 4

HCID 961HydroxideHCID 199401P,P-Diphenylphosphinic azideHCID 5360545SodiumHCID 58355160HCID 58355160, compound

Product 1

HCID 58355545HCID 58355545, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8471TriethylamineSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
100 °C

Procedure

(3R,5S)-1-(tert-Butoxycarbonyl)-5-[{[5-(4-methoxybutyl)-1-phenyl-1H-1,2,3-triazol-4-yl]carbonyl}(2-methylpropyl)amino]piperidine-3-carboxylic acid (250 mg) was dissolved in toluene (5 ml), diphenylphosphoryl azide (0.15 ml) and triethylamine (94 μl) were added and the mixture was stirred at 100° C. for 2 hr. The reaction mixture was cooled to room temperature, 8M aqueous sodium, hydroxide solution (0.56 ml) was added and the mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate and the mixture was extracted twice with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was subjected to basic silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (1:1-1:0) and ethyl acetate-methanol (10:1) was concentrated under reduced pressure to give the object product (155 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringthe mixture was stirred at room temperature for 1 hr
  3. extractionthe mixture was extracted twice with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. washa fraction eluted with ethyl acetate-hexane (1:1-1:0) and ethyl acetate-methanol (10:1)
  7. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-df26c3e4d383439b96b7e5a417e0a4d8
Source dataset
uspto-grants-2014_03
Patent number
US08664380B2

Reaction notes

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