5-Aminovaleric acid → HCID 19808302, compound

HRID 1577045Notes

Reaction equation

HRID 1577045 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7].CN(C)C(=N)N(C)C.[C:17]([O:21][C:22](N=[N+]=[N-])=[O:23])([CH3:20])([CH3:19])[CH3:18]>CN(C)C=O>[C:17]([O:21][C:22]([CH:5]([CH2:4][CH2:3][CH2:2][NH2:1])[C:6]([OH:8])=[O:7])=[O:23])([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 1385-Aminovaleric acidHCID 61256Carbonazidic acid, 1,1-dimethylethyl esterHCID 664601,1,3,3-Tetramethylguanidine

Product 1

HCID 19808302HCID 19808302, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Amino pentanoic acid (0.585 g, 5 m mol) was stirred for two days in dimethylformamide (5 ml) containing tetramethylguanidine (1.14 g, 10 m mol) and tert.butoxycarbonylazide (1.1 g, 7.5 m mol). The solution was evaporated and the residue partitioned between ethyl acetate (20 ml) and 10% citric acid solution (20 ml). The organic layer was washed with 10% citric acid (2×15 ml), water (3×15 ml) and brine (1×15 ml). Each aqueous wash was back extracted with ethyl acetate (20 ml). The combined organic layers were dried over anhydrous magnesium sulphate and evaporated to give an oil which slowly crystallised. Recrystallisation from diisopropyl ether/petrol gave 0.745 g (70% yield), mp. 47.5°-48.5° C., Rf silica gel 0.40 (benzene:dioxan:acetic acid 95:75:4).

Workup

  1. customThe solution was evaporated
  2. customthe residue partitioned between ethyl acetate (20 ml) and 10% citric acid solution (20 ml)
  3. washThe organic layer was washed with 10% citric acid (2×15 ml), water (3×15 ml) and brine (1×15 ml)
  4. washEach aqueous wash
  5. extractionwas back extracted with ethyl acetate (20 ml)
  6. dry with materialThe combined organic layers were dried over anhydrous magnesium sulphate
  7. customevaporated
  8. customto give an oil which
  9. customslowly crystallised
  10. customRecrystallisation from diisopropyl ether/petrol
  11. customgave 0.745 g (70% yield), mp. 47.5°-48.5° C., Rf silica gel 0.40 (benzene:dioxan:acetic acid 95:75:4)

Sources & evidence

ORD record
ord-f10c65df8d534fc794668254ba774c5d
Source dataset
uspto-grants-1981_09
Patent number
USRE030731

Reaction notes

Loading…