Triethylamine → HCID 86761173, compound

HRID 1713552Notes

Reaction equation

HRID 1713552 reaction equation
[C:1]1([C:7]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]3[CH2:12][NH:13][CH2:14][CH2:15][N:10]3[C:9](=[O:16])[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:23]([O:27][C:28]([NH:30][CH2:31][C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][CH:40]=1)[C:35](O)=[O:36])=[O:29])([CH3:26])([CH3:25])[CH3:24].ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C>C(#N)C.O.C(OCC)(=O)C>[O:16]=[C:9]1[N:10]2[CH2:15][CH2:14][N:13]([C:35]([C:34]3[CH:33]=[C:32]([CH2:31][NH:30][C:28](=[O:29])[O:27][C:23]([CH3:25])([CH3:24])[CH3:26])[CH:40]=[CH:39][CH:38]=3)=[O:36])[CH2:12][CH:11]2[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[O:8]1

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27559293-(((tert-Butoxycarbonyl)amino)methyl)benzoic acidHCID 231218811,1-Diphenyltetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one

Product 1

HCID 86761173HCID 86761173, compoundYield 76.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-one (0.20 g, 0.67 mmol), 3-[[(tert-butoxycarbonyl)amino]methyl]benzoic acid (0.17 g, 0.67 mmol), 1-hydroxybenzotriazole (0.10 g, 0.74 mmol) and triethylamine (69 mg, 0.68 mmol) in acetonitrile (10 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.20 g, 1.0 mmol), and the mixture was stirred at room temperature for 15 hours. To the reaction solution were added ethyl acetate and water. The separated organic layer was washed with saturated brine, dried over sodium sulfate, and then concentrated. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=3:1 to 3:7) to obtain the title compound (0.27 g, yield 75%).

Workup

  1. washThe separated organic layer was washed with saturated brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=3:1 to 3:7)

Sources & evidence

ORD record
ord-96f8deed896a4b72a431f966db60d990
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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