Triethylamine → HCID 67409016, compound

HRID 1174149Notes

Reaction equation

HRID 1174149 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C@@H:5]([C@@H:13]([CH3:16])[CH2:14][CH3:15])[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[CH3:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][N:19]=1.[BH4-].[Na+].C1C(=O)N(OC(ON2C(=O)CCC2=O)=O)[C:30](=[O:31])C1.C(N(CC)CC)C>C1C=CC=CC=1.C(O)C.ClCCCl>[CH3:16][C@@H:13]([CH2:14][CH3:15])[C@H:5]([N:4]1[CH2:3][CH2:2][N:1]([CH2:22][C:21]2[CH:20]=[N:19][C:18]([CH3:17])=[CH:25][CH:24]=2)[C:30]1=[O:31])[C:6]([O:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:7]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 676246Di(succinimido) carbonateHCID 4311764Sodium borohydrideHCID 101925666-Methyl-3-pyridinecarboxaldehydeHCID 86598803tert-butyl(2S,3S)-2-[(2-aminoethyl)amino]-3-methylpentanoate

Product 1

HCID 67409016HCID 67409016, compoundYield 49.5%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 241BenzeneSolventHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A solution containing the product from Example 3G (0.55 g, 2.39 mmol) in a mixture of benzene (6 mL) and ethanol (6 mL) was treated with the product from Example 13A (0.265 g, 2.19 mmol), stirred at 70° C. for 2 hours, cooled to 25° C., treated with sodium borohydride (0.25 g, 6.61 mmol), stirred at 25° C. for 3 hours, and partitioned between ethyl acetate and saturated NaHCO3. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated. A solution of the residue (2.19 mmol) in 1,2-dichloroethane (90 mL) was treated with N,N-disuccinimidyl carbonate (0.675 g, 2.63 mmol) and triethylamine (0.30 mL, 2.15 mmol), stirred at 25° C. for 16 hours, and partitioned with 10% NaCO3. The aqueous phase was extracted with additional dichloromethane. The combined organic phase was dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 0-100% ethyl acetate/dichloromethane to give the title compound (0.392 g, 49% yield).

Workup

  1. temperaturecooled to 25° C.
  2. stirringstirred at 25° C. for 3 hours
  3. custompartitioned between ethyl acetate and saturated NaHCO3
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. stirringstirred at 25° C. for 16 hours
  9. custompartitioned with 10% NaCO3
  10. extractionThe aqueous phase was extracted with additional dichloromethane
  11. dry with materialThe combined organic phase was dried over MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customThe residue was chromatographed on silica gel eluting with 0-100% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-4b22312ba3034ddfb9989f9296e9f17f
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

Loading…