Sodium Bicarbonate → HCID 89668523, compound

HRID 1482336Notes

Reaction equation

HRID 1482336 reaction equation
[C:1](=[O:23])(OC1C=CC([N+]([O-])=O)=CC=1)[O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]=[N+:11]=[N-:12].[NH:24]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C@H:25]([C:31]([OH:33])=[O:32])[CH2:26][CH2:27][CH2:28][CH2:29][NH2:30].C(=O)(O)[O-].[Na+].S(=O)(=O)(O)[O-].[K+]>O1CCOCC1.C(OCC)(=O)C.O>[N:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:3][O:2][C:1]([NH:30][CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]([NH:24][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:31]([OH:33])=[O:32])=[O:23])=[N+:11]=[N-:12]

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 516920Potassium bisulfateHCID 2733284epsilon-tert-Butyloxycarbonyl-lysineHCID 89668497HCID 89668497, compound

Product 1

HCID 89668523HCID 89668523, compoundYield 85.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

2-Azidobenzyl (4-nitrophenyl) carbonate (414 mg, 1.317 mmol) was added to a suspension of Boc-Lys-OH (Compound tk39) (295 mg, 1.198 mmol) and sodium bicarbonate (252 mg, 2.99 mmol) in 1,4-dioxane (3 mL)-water (2 mL). The reaction mixture was stirred at room temperature for 22 hours and then cooled in an ice bath and diluted with ethyl acetate and water, and a saturated aqueous potassium bisulfate solution (0.7 mL) was added to the resulting mixture. The mixture was extracted with ethyl acetate (×2), and the organic phase was washed with water (10 mL×2) and brine (10 mL) and dried over sodium sulfate. Following concentration under reduced pressure, the resulting crude product was purified by normal-phase silica gel column chromatography (hexane/ethyl acetate) to afford (S)-6-((((2-azidobenzyl)oxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)hexanoic acid (Compound tk40) (431.5 mg, 85%).

Workup

  1. temperaturecooled in an ice bath
  2. extractionThe mixture was extracted with ethyl acetate (×2)
  3. washthe organic phase was washed with water (10 mL×2) and brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentration under reduced pressure
  6. customthe resulting crude product was purified by normal-phase silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0df7f6fdf6654020b0712538e0f5e07c
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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