3,3,3-Triphenylpropionic Acid → Ethyl 3-(2-{(3,3,3-triphenylpropanoyl)amino}acetylamino)propionate

HRID 394007Notes

Reaction equation

HRID 394007 reaction equation
Cl.[NH2:2][CH2:3][C:4]([NH:6][CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:5].[C:14]1([C:20]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:21][C:22](O)=[O:23])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)(Cl)Cl.C(OCC)(=O)C.C(N(CC)CC)C>[C:31]1([C:20]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:21][C:22]([NH:2][CH2:3][C:4]([NH:6][CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:5])=[O:23])[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

8

Reactant 4

HCID 1366963,3,3-Triphenylpropionic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 22647362Ethyl 3-{(2-aminoacetyl)amino}propionate monohydrochloride

Product 1

HCID 22647252Ethyl 3-(2-{(3,3,3-triphenylpropanoyl)amino}acetylamino)propionateYield 51.4%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.52 g of ethyl 3-{(2-aminoacetyl)amino}propionate monohydrochloride and 2.18 g of 3,3,3-triphenylpropionic acid in 20 ml of chloroform, 1.46 g of 1-hydroxybenzotriazole monohydrate, 2.07 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide monohydrochloride and 2.0 ml of triethylamine were successively added at room temperature by the order stated, followed by 2 hours' stirring at the same temperature. The reaction liquid: was diluted with ethyl acetate and washed successively with aqueous saturated sodium bicarbonate solution, 1N-hydrochloric acid and water, and filtered through cerite. The filtrate was dried on anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resultant residue was purified by means of silica gel column chromatography (eluting solvent: hexane/ethyl acetate=4/1-chloroform/methanol=10/1) to provide 1.7 g of the title compound.

Workup

  1. customThe reaction liquid
  2. washwashed successively with aqueous saturated sodium bicarbonate solution, 1N-hydrochloric acid and water
  3. filtrationfiltered through cerite
  4. dry with materialThe filtrate was dried on anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resultant residue was purified by means of silica gel column chromatography (eluting solvent: hexane/ethyl acetate=4/1-chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-e8fce23bd7c24ed0a3748355fb8a24e5
Source dataset
uspto-grants-2004_10
Patent number
US06809108B1

Reaction notes

Loading…