Triethylamine → HCID 59853920, compound

HRID 2374820Notes

Reaction equation

HRID 2374820 reaction equation
Cl.C(N=C=NCCCN(C)C)C.[CH3:13][NH:14][CH2:15][CH2:16][CH2:17][CH:18]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[CH:26]=[CH:25][C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]1=2.Cl.C(N(CC)CC)C.[C:41]([O:45][C:46]([NH:48][CH2:49][C:50]([OH:52])=O)=[O:47])([CH3:44])([CH3:43])[CH3:42].C(=O)([O-])O.[Na+]>ClCCl>[CH:32]1[C:27]2[CH:26]=[CH:25][C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH:18]([CH2:17][CH2:16][CH2:15][N:14]([CH3:13])[C:50](=[O:52])[CH2:49][NH:48][C:46](=[O:47])[O:45][C:41]([CH3:42])([CH3:43])[CH3:44])[C:28]=2[CH:29]=[CH:30][CH:31]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6603149Protriptyline hydrochloride

Product 1

HCID 59853920HCID 59853920, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

134 mg (0.70 mmol) of 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride, 176 mg (0.59 mmol) of protriptyline hydrochloride and 0.176 ml (1.26 mmol) of triethylamine were added to 129 mg (0.74 mmol) of t-butoxycarbonylglycine in 5 ml of dichloromethane, and they were stirred at room temperature overnight. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture. After extracting with dichloromethane, the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane:ethyl acetate=3:1) to obtain the title compound.

Workup

  1. extractionAfter extracting with dichloromethane
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by the silica gel chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-0e900a9b56b64013b2529e6e0c3f6f6f
Source dataset
uspto-grants-2008_12
Patent number
US07462630B2

Reaction notes

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