Sodium Bicarbonate → HCID 89668382, compound

HRID 1482320Notes

Reaction equation

HRID 1482320 reaction equation
[NH2:1][C@@H:2]([CH2:6][CH2:7][C@H:8]([S:11][S:12][CH3:13])[CH2:9][NH2:10])[C:3]([OH:5])=[O:4].C(=O)(O)[O-].[Na+].[C:19](=O)([O:31]C1C=CC([N+]([O-])=O)=CC=1)[O:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]=[N+:29]=[N-:30])=[CH:24][CH:23]=1.C(N(CC([O-])=O)CC([O-])=O)CN(CC(O)=O)CC(O)=O.[Na+].[Na+]>O.CC(C)=O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[NH2:1][C@@H:2]([CH2:6][CH2:7][C@H:8]([S:11][S:12][CH3:13])[CH2:9][NH:10][C:19]([O:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([N:28]=[N+:29]=[N-:30])=[CH:26][CH:27]=1)=[O:31])[C:3]([OH:5])=[O:4]

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 11809184HCID 11809184, compoundHCID 13020083Ethylenediaminetetraacetic acid disodium saltHCID 89668381HCID 89668381, compound

Product 1

HCID 89668382HCID 89668382, compoundYield 16%

Reagents, catalysts & solvents 3

HCID 24463Copper sulfate pentahydrateCatalystHCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

A solution of copper sulfate pentahydrate (100 mg, 0.4 mmol) in water (0.3 mL) was added to a solution of (2S,5S)-2,6-diamino-5-(methyldisulfanyl)hexanoic acid (Compound tk6) (176 mg, 0.785 mol) and sodium bicarbonate (659 mg, 7.85 mmol) in water (1.2 mL) at room temperature, followed by addition of a solution of 4-azidobenzyl (4-nitrophenyl) carbonate synthesized by the method described in the literature (Bioconjugate Chem. 2008, 19, 714) (296 mg, 0.941 mmol) in acetone (2.7 mL). The reaction mixture was stirred at the same temperature for 25.75 hours and then filtered, and the solid on the filter paper was washed with water. The solid collected by filtration was suspended in water (10 mL)-methanol (1 mL), followed by addition of disodium dihydrogen ethylenediaminetetraacetate (350 mg, 0.941 mmol) at room temperature. The reaction mixture was stirred at the same temperature for 7.75 hours and then filtered, and the white solid on the filter paper was purified by reverse-phase silica gel column chromatography (10 mM ammonium acetate aqueous solution/methanol) to afford (2S,5S)-2-amino-6-((((4-azidobenzyl)oxy)carbonyl)amino)-5-(methyldisulfanyl)hexanoic acid (Lys(5S-SSMe)(Acbz)) (Compound tk7) (50.2 mg, 16%).

Workup

  1. customsynthesized by the method
  2. filtrationfiltered
  3. washthe solid on the filter paper was washed with water
  4. filtrationThe solid collected by filtration
  5. stirringThe reaction mixture was stirred at the same temperature for 7.75 hours
  6. filtrationfiltered
  7. customthe white solid on the filter paper was purified by reverse-phase silica gel column chromatography (10 mM ammonium acetate aqueous solution/methanol)

Sources & evidence

ORD record
ord-3238bd4dfa714520b3719b4f71925917
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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