Sodium Chloride → HCID 178502729, compound

HRID 1506133Notes

Reaction equation

HRID 1506133 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([C:19]([OH:21])=O)[CH2:15][CH2:14]1.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+].Cl.[CH3:31][NH:32][O:33][CH3:34].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[Cl-].[Na+]>O.C(Cl)(Cl)Cl.C(OCC)(=O)C>[CH3:34][O:33][N:32]([CH3:31])[C:19]([C@H:16]1[CH2:17][CH2:18][C@H:13]([NH:12][C:2](=[O:3])[O:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:14][CH2:15]1)=[O:21]

Participants

13

Reactant 9

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178511567HCID 178511567, compound

Product 1

HCID 178502729HCID 178502729, compoundYield 26%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzyl chloroformate (885 μL, 6.30 mmol) was gradually added dropwise to trans-4-aminocyclohexanecarboxylic acid (600 mg, 4.20 mmol) and sodium carbonate (891 mg, 8.40 mmol) in water (12 mL) under cooling with ice, and the reaction mixture was stirred for one day. After addition of 1 M aqueous sodium hydroxide and ethyl acetate, the insoluble solid was collected by filtration to give a colorless solid. The solid was dissolved in chloroform (10 mL) and stirred with N,O-dimethylhydroxylamine hydrochloride (416 mg, 4.27 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (819 mg, 4.27 mmol), 1-hydroxybenzotriazole (577 mg, 4.27 mmol) and triethylamine (892 μL, 6.40 mmol) at room temperature for one day. After addition of water and saturated aqueous sodium chloride, the reaction mixture was extracted with chloroform, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1 (v/v)) to give the title compound as a colorless solid (350 mg, yield 26%).

Workup

  1. temperatureunder cooling with ice
  2. filtrationthe insoluble solid was collected by filtration
  3. customto give a colorless solid
  4. extractionthe reaction mixture was extracted with chloroform
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1 (v/v))

Sources & evidence

ORD record
ord-eec2f3ea4dc446c088a2fcc233fc3d49
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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