Triethylamine → HCID 66679862, compound

HRID 1626734Notes

Reaction equation

HRID 1626734 reaction equation
C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C.[O:20]1[CH:24]=[CH:23][C:22]([C:25]2[CH:26]=[C:27]([CH2:31][C:32]([OH:34])=O)[CH:28]=[CH:29][CH:30]=2)=[CH:21]1.Cl.[Cl:36][C:37]1[CH:38]=[CH:39][C:40]([NH:47][C:48](=[O:54])[C@@H:49]2[CH2:53][CH2:52][CH2:51][NH:50]2)=[C:41]([CH:46]=1)[C:42]([O:44][CH3:45])=[O:43].ON1C2C=CC=CC=2N=N1>C(OCC)(=O)C.O.CC(N(C)C)=O>[Cl:36][C:37]1[CH:38]=[CH:39][C:40]([NH:47][C:48](=[O:54])[C@@H:49]2[CH2:53][CH2:52][CH2:51][N:50]2[C:32](=[O:34])[CH2:31][C:27]2[CH:28]=[CH:29][CH:30]=[C:25]([C:22]3[CH:23]=[CH:24][O:20][CH:21]=3)[CH:26]=2)=[C:41]([CH:46]=1)[C:42]([O:44][CH3:45])=[O:43]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22326463HCID 22326463, compoundHCID 66680322HCID 66680322, compound

Product 1

HCID 66679862HCID 66679862, compoundYield 88.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

Under ice-cooling, 0.096 mL (0.690 mmol) of triethylamine and 144 mg (0.752 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride were added while stirring to a DMAc (5 mL) solution comprising 127 mg (0.627 mmol) of [3-(furan-3-yl)phenyl]acetic acid, 200 mg (0.627 mmol) of methyl 5-chloro-2-(L-prolylamino)benzoate hydrochloride, and 102 mg (0.752 mmol) of 1-hydroxybenzotriazole; and the mixture was stirred overnight. After water and ethyl acetate were added to the reaction mixture and the mixture was stirred, the organic layer was separated and washed with saturated sodium bicarbonate water, 0.1% hydrochloric acid, and saturated saline, followed by drying over sodium sulfate, filtration, and condensation. The crude product was purified by silica gel chromatography (n-hexane/ethyl acetate=4/1→2/1→1/1), thereby giving 258 mg of methyl 5-chloro-2-[(1-{[3-(furan-3-yl)phenyl]acetyl}-L-prolyl)amino]benzoate (yield: 88%).

Workup

  1. temperatureUnder ice-cooling
  2. stirringthe mixture was stirred
  3. customthe organic layer was separated
  4. washwashed with saturated sodium bicarbonate water, 0.1% hydrochloric acid, and saturated saline
  5. dry with materialby drying over sodium sulfate, filtration, and condensation
  6. customThe crude product was purified by silica gel chromatography (n-hexane/ethyl acetate=4/1→2/1→1/1)

Sources & evidence

ORD record
ord-e87bebcd9fc3498b9e8f03a577ef56a6
Source dataset
uspto-grants-2014_07
Patent number
US08785473B2

Reaction notes

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