Triethylamine → HCID 137231661, compound

HRID 1683940Notes

Reaction equation

HRID 1683940 reaction equation
[C:1]([NH:4][C@H:5]1[C@H:13]([C@@H:14]([C@@H:16]([CH2:18][OH:19])[OH:17])[OH:15])[O:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C@@H:6]1[NH2:20])(=[O:3])[CH3:2].C(N(CC)CC)C.CS[C:30](=[NH:35])[NH:31][N+:32]([O-:34])=[O:33]>CO>[C:1]([NH:4][C@H:5]1[C@H:13]([C@@H:14]([C@@H:16]([CH2:18][OH:19])[OH:17])[OH:15])[O:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C@@H:6]1[NH:20][C:30]([NH2:35])=[N:31][N+:32]([O-:34])=[O:33])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 445533130525-62-1HCID 135927615N-Nitro-S-methylisothiourea

Product 1

HCID 137231661HCID 137231661, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

5-(Acetylamino)-4-amino-2,6-anhydro-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid (200 mg, 0.689 mmol) was dissolved in absolute methanol (2.7 ml) by the addition of triethylamine (0.098 ml, 0.690 mmol). 2-Methyl-1-nitro-2-thiopseudourea (103 mg,0.757 mmol) was then added. The mixture was warmed to 40° C. with stirring under nitrogen for 2hrs, then stirred at 21° C. for 16 hr. The addition of reagent and heating and stirring was repeated twice more. The cooled mixture was then filtered and the white solid washed with methanol. Combined filtrate and washings were evaporated and the residue purified by ion exchange chromatography (Dowex 50 W×8(H+) resin, eluting with water. Appropriate fractions were combined and freeze dried. The residue was triturated with warm water (4 ml), and the off-white solid filtered and dried under high vacuum to give the title product (Yield =50 mg).

Workup

  1. stirringstirred at 21° C. for 16 hr
  2. additionThe addition of reagent
  3. temperatureheating
  4. stirringstirring
  5. filtrationThe cooled mixture was then filtered
  6. washthe white solid washed with methanol
  7. customCombined filtrate and washings were evaporated
  8. customthe residue purified by ion exchange chromatography (Dowex 50 W×8(H+) resin
  9. washeluting with water
  10. customfreeze dried
  11. customThe residue was triturated with warm water (4 ml)
  12. filtrationthe off-white solid filtered
  13. customdried under high vacuum

Sources & evidence

ORD record
ord-c2657d9d34bf415092bd3b44d13d3738
Source dataset
uspto-grants-1997_06
Patent number
US05639786

Reaction notes

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