Dimethyl Sulfide → HCID 131730902, compound

HRID 1041822Notes

Reaction equation

HRID 1041822 reaction equation
[CH:1]([OH:14])([CH:9]([OH:13])[C:10]([OH:12])=[O:11])[CH:2]([OH:8])[CH:3]([OH:7])[C:4]([OH:6])=[O:5].[NH3:15].N.COC(=N)CCCCCCC(=[NH:29])OC.[CH3:31][S:32][CH3:33]>C([O-])(O)=O.[Na+].O>[CH:1]([OH:14])([CH:9]([OH:13])[C:10]([OH:12])=[O:11])[CH:2]([OH:8])[CH:3]([OH:7])[C:4]([OH:6])=[O:5].[NH3:29].[NH3:15].[CH3:31][S:32][CH3:33]

Participants

6

Reactant 3

HCID 1068Dimethyl SulfideHCID 34750Dimethyl SuberimidateHCID 101747Diammonium meso-galactarate

Product 1

HCID 131730902HCID 131730902, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A 1.5 mL eppendorff tube was charged with a solution of 85.5 mg (0.233 mmol) of the bis(hydrochloride) salt of Example 3 (3) in 0.8 mL of 0.1 M NaHCO3. Dimethylsuberimidate.2HCl (DMS, Pierce Chemical Co., 63.6 mg, 0.233 mmol) was added and the solution was vortexed and centrifuged to dissolve the components. The resulting mixture was stirred at room temperature for 15 h. The mixture was then diluted to 8 mL with water and the pH was brought to 4 with the addition of 1 NHCl. This solution was then dialyzed with a 3500 MWCO dialysis membrane (Pierce pleated dialysis tubing) in ddH2O for 24 h. The dialyzed solution was lyophilized to dryness to give 49 mg of a white fluffy powder. 1H NMR (500 MHz, dDMSO) δ 9.15 (bs), 7.92 (bs), 5.43 (bs), 4.58 (bs), 4.17 (bs), 3.82 (bs), 3.37 (bs), 3.28 (bs), 2.82 (bs), 2.41 (bs), 1.61 (bs), 1.28 (bs). 13C NMR (126 MHz, dDMSO) δ 174.88 (s, 1H), 168.38 (s, 1H), 71.45 (s, 4H), 71.22 (s, 3H), 42.34 (s, 2H), 36.96 (s, 3H), 32.74 (s, 3H), 28.09 (s, 4H), 26.90 (s, 4H). Mw [GPC]=2520, Mw/Mn=1.15.

Workup

  1. dissolutionto dissolve the components
  2. additionthe pH was brought to 4 with the addition of 1 NHCl
  3. customThis solution was then dialyzed with a 3500 MWCO dialysis membrane (Pierce pleated dialysis tubing) in ddH2O for 24 h
  4. customto give 49 mg of a white fluffy powder

Sources & evidence

ORD record
ord-7a30c0fa41db4d1a9d1ccff827610190
Source dataset
uspto-grants-2013_10
Patent number
US08557292B2

Reaction notes

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