Hydrochloric Acid → HCID 23500279, compound

HRID 1835876Notes

Reaction equation

HRID 1835876 reaction equation
C1(C)C=CC(S([N:10]([CH2:20][CH2:21][N:22](S(C2C=CC(C)=CC=2)(=O)=O)[CH2:23][CH2:24][N:25](S(C2C=CC(C)=CC=2)(=O)=O)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][N:35](S(C2C=CC(C)=CC=2)(=O)=O)[CH2:36][CH2:37][N:38](S(C2C=CC(C)=CC=2)(=O)=O)[CH2:39][CH2:40][N:41](S(C2C=CC(C)=CC=2)(=O)=O)[CH2:42][CH3:43])[CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][OH:19])(=O)=O)=CC=1.[Na+].[Na+].P(=O)(O)([O-])[O-].Cl>CO.O1CCOCC1>[CH2:18]([OH:19])[CH2:17][O:16][CH2:15][CH2:14][O:13][CH2:12][CH2:11][NH:10][CH2:20][CH2:21][NH:22][CH2:23][CH2:24][NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH:35][CH2:36][CH2:37][NH:38][CH2:39][CH2:40][NH:41][CH2:42][CH3:43]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24203Sodium Phosphate, DibasicHCID 23500281HCID 23500281, compound

Product 1

HCID 23500279HCID 23500279, compound

Reagents, catalysts & solvents 1

HCID 21966525Dioxane MethanolSolvent

Procedure

A mixture of 9,12,15,25,28,31-hexa(p-toluenesulfonyl)-9,12,15,25,28,31-hexaaza-3,6-dioxatritriacontanol (1.30 g, 0.92 mmole), Na/Hg (10.85 g), and phosphoric acid disodium salt (1.96 g, 13.8 mmole) in methanol/dioxane (70 ml/40 ml) was heated to gentle reflux for 24 hours. Additional Na/Hg (2.0 g) was then added. The reaction mixture was maintained at reflux for another 24 hours, then cooled. The insoluble material was filtered and washed with CH3OH. The filtrate was concentrated to give an oily residue which was then treated with 2 N HCl (aq) and washed with CH2Cl2 (200 ml×2). The aqueous acidic solution was then made basic with 10% NaOH (aq), extracted with CH2Cl2 (250 ml×3), dried over MgSO4, filtered and concentrated to give a pale yellow oil (0.25 g, 55% crude yield) which was used further without purification. The reaction is shown schematically below:

Workup

  1. temperaturewas heated
  2. temperatureto gentle reflux for 24 hours
  3. additionAdditional Na/Hg (2.0 g) was then added
  4. temperatureThe reaction mixture was maintained
  5. temperatureat reflux for another 24 hours
  6. temperaturecooled
  7. filtrationThe insoluble material was filtered
  8. washwashed with CH3OH
  9. concentrationThe filtrate was concentrated
  10. customto give an oily residue which
  11. washwashed with CH2Cl2 (200 ml×2)
  12. extractionextracted with CH2Cl2 (250 ml×3)
  13. dry with materialdried over MgSO4
  14. filtrationfiltered
  15. concentrationconcentrated
  16. customto give a pale yellow oil (0.25 g, 55% crude yield) which
  17. customwas used further without purification

Sources & evidence

ORD record
ord-1646d29840614ad2b6ed6e707ffbce45
Source dataset
uspto-grants-2004_08
Patent number
US06774082B2

Reaction notes

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