Acetone → HCID 178512927, compound

HRID 1180678Notes

Reaction equation

HRID 1180678 reaction equation
[CH2:1]([S:11]([OH:14])(=[O:13])=[O:12])[CH2:2][S:3][S:4][CH2:5][CH2:6][S:7]([OH:10])(=[O:9])=[O:8].[NH2:15][C@H:16]([C:24]([OH:26])=[O:25])[CH2:17][CH2:18][CH2:19][NH:20][C:21](=[NH:23])[NH2:22].CC(C)=O>O>[CH2:1]([S:11]([OH:14])(=[O:13])=[O:12])[CH2:2][S:3][S:4][CH2:5][CH2:6][S:7]([OH:10])(=[O:8])=[O:9].[NH2:15][C@H:16]([C:24]([OH:26])=[O:25])[CH2:17][CH2:18][CH2:19][NH:20][C:21](=[NH:22])[NH2:23].[NH2:15][C@H:16]([C:24]([OH:26])=[O:25])[CH2:17][CH2:18][CH2:19][NH:20][C:21](=[NH:22])[NH2:23]

Participants

5

Reactant 3

HCID 180AcetoneHCID 656262,2'-Dithiodiethanesulfonic acidHCID 178418600HCID 178418600, compound2×

Product 1

HCID 178512927HCID 178512927, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2,2′-dithiobis ethane sulfonic acid (2.5 g, containing 9% water, 8.1 mmol) in water (1.0 mL) was titrated with L-Arginine (98% purity, Aldrich) aqueous solution until the pH of the reaction solution was adjusted to 7.0. Overall 2.80 g of L-arginine was used. Acetone was added to precipitate the product. The product in aqueous solution was dried under high vacuum to remove as much water as possible. The residue was resuspended in ethanol (30 mL). The white precipitate was isolated by filtration, washed with ethanol (2×30 mL), dried to give 4.93 g of product (97% yield). The purity of the product was 96.3% from HPLC analysis.

Workup

  1. customto precipitate the product
  2. customThe product in aqueous solution was dried under high vacuum
  3. customto remove as much water as possible
  4. customThe white precipitate was isolated by filtration
  5. washwashed with ethanol (2×30 mL)
  6. customdried

Sources & evidence

ORD record
ord-5c94af5d034c4ad4a669720239bc1926
Source dataset
uspto-grants-2007_10
Patent number
US07282602B2

Reaction notes

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