Triethylamine → HCID 60007028, compound

HRID 1506141Notes

Reaction equation

HRID 1506141 reaction equation
C(N(CC)CC)C.[CH2:8]([O:15][C:16]([N:18]1[CH2:22][CH2:21][CH:20]([C:23]([OH:25])=O)[CH2:19]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl.[CH3:27][NH:28][O:29][CH3:30].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>C(Cl)(Cl)Cl.O>[CH3:30][O:29][N:28]([CH3:27])[C:23]([CH:20]1[CH2:21][CH2:22][N:18]([C:16]([O:15][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[O:17])[CH2:19]1)=[O:25]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 185384831-N-Cbz-pyrrolidine-3-carboxylic acid

Product 1

HCID 60007028HCID 60007028, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

Triethylamine (1.68 mL, 12.0 mmol) was added dropwise to 1-[(benzyloxy)carbonyl]pyrrolidine-3-carboxylic acid (1.00 g, 4.01 mmol), N,O-dimethylhydroxylamine hydrochloride (782 mg, 8.02 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.54 g, 8.02 mmol) and 1-hydroxybenzotriazole (1.08 g, 8.02 mmol) in chloroform (20 mL), and the reaction mixture was stirred at room temperature for 16 hours. After addition of water, the reaction mixture was extracted with chloroform, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1→3/7 (v/v)) to give the title compound as a yellow oil (1.11 g, yield 95%).

Workup

  1. extractionthe reaction mixture was extracted with chloroform
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1→3/7 (v/v))

Sources & evidence

ORD record
ord-6d36fda4ebc44d888074e4302cf1766b
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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