Butylamine → HCID 89806708, compound

HRID 1474588Notes

Reaction equation

HRID 1474588 reaction equation
[CH2:1]([O:8][C:9](=[O:23])[CH2:10][C@@H:11]([C:20]([OH:22])=O)[NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:24]([NH2:28])[CH2:25][CH2:26][CH3:27].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[CH2:1]([O:8][C:9](=[O:23])[CH2:10][C@@H:11]([C:20]([NH:28][CH2:24][CH2:25][CH2:26][CH3:27])=[O:22])[NH:12][C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8007ButylamineHCID 757711-HydroxybenzotriazoleHCID 1581888N-tert-Butoxycarbonyl-L-aspartic acid beta-benzyl esterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 89806708HCID 89806708, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4.27 g of N-(tert-butoxycarbonyl)aspartic acid-4-benzyl ester and 1.31 mL of n-butyl amine were dissolved in 25 mL of DMF, and then 2.93 g of WSC hydrochloride and 1.93 g of HOBt were added thereto, and the reaction solution was stirred at room temperature overnight. The reaction solution was added with water, and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of ammonium chloride and a saturated aqueous solution of sodium hydrogen carbonate, dried with magnesium sulfate, and then distilled under reduced pressure to remove ethyl acetate, and then dried under vacuum, thereby to give 5.12 g of Compound 6.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of ammonium chloride
  3. dry with materiala saturated aqueous solution of sodium hydrogen carbonate, dried with magnesium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove ethyl acetate
  6. customdried under vacuum

Sources & evidence

ORD record
ord-75f32024140c453e813a76d836e251da
Source dataset
uspto-grants-2015_04
Patent number
US09018323B2

Reaction notes

Loading…