Sodium Bicarbonate → HCID 89668503, compound

HRID 1482324Notes

Reaction equation

HRID 1482324 reaction equation
FC(F)(F)[C:3]([O-:5])=[O:4].[C:8]([C@@H:11]([NH3+:20])[CH2:12][CH2:13][C@H:14]([S:17](C)=[S:18])[CH2:15][NH3+:16])([OH:10])=[O:9].F[C:22](F)(F)C([O-])=O.C(=O)(O)[O-].[Na+].C(=O)([O-])OC1C=CC([N+]([O-])=O)=CC=1[CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[N:51]=[N+:52]=[N-:53].C(N(CC([O-])=O)CC([O-])=O)CN(CC(O)=O)CC(O)=O.[Na+].[Na+]>O.C(#N)C.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[NH2:20][C@@H:11]([CH2:12][CH2:13][C@H:14]([S:17][S:18][CH3:22])[CH2:15][NH:16][C:3]([O:5][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[N:51]=[N+:52]=[N-:53])=[O:4])[C:8]([OH:10])=[O:9]

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 13020083Ethylenediaminetetraacetic acid disodium saltHCID 117736178HCID 117736178, compoundHCID 117953053HCID 117953053, compound

Product 1

HCID 89668503HCID 89668503, compoundYield 15%

Reagents, catalysts & solvents 3

HCID 24463Copper sulfate pentahydrateCatalystHCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

A solution of copper sulfate pentahydrate (63.6 mg, 0.255 mmol) in water (0.3 mL) was added to a solution of (1S,4S)-1-carboxy-4-(methylsulfinothioyl)pentane-1,5-diaminium 2,2,2-trifluoroacetate synthesized by the method described in the literature (J. Am. Chem. Soc. 2011, 133, 10708) (Compound tk1) (226 mg, 0.50 mmol) and sodium bicarbonate (420 mg, 5.00 mmol) in water (1.2 mL) at room temperature, followed by addition of a solution of 2-azidobenzyl(4-nitrophenyl) carbonate (Compound tk13) (188 mg, 0.599 mmol) in acetonitrile (6 mL). The reaction mixture was stirred at the same temperature for 49 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 (223 mg, 0.599 mmol) at room temperature. The reaction mixture was stirred at the same temperature for 17.25 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-((((2-azidobenzyl)oxy)carbonyl)amino)-5-(methyldisulfanyl)hexanoic acid (Lys(5S-SSMe)(oAcbz)) (Compound tk14) (30.2 mg, 15%).

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 17.25 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-26406c0f417c49f19176a8757f98f45f
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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