Triethylamine → HCID 68684193, compound

HRID 657175Notes

Reaction equation

HRID 657175 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH:3]1[C:15]([OH:17])=O.C([N:20](CC)CC)C.ON1C2N=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(=O)(O)[O-].[NH4+]>CN(C)C=O>[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH:3]1[C:15]([NH2:20])=[O:17]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 14013Ammonium BicarbonateHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 20502081HCID 20502081, compound

Product 1

HCID 68684193HCID 68684193, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxy-1-(phenylmethyl)-3-piperidinecarboxylic acid (12 g) and triethylamine (3.53 mL, 25.5 mmol) in N,N-dimethylformamide (60 mL) was added 1-hydroxy-7-azabenzotriazole (3.48 g, 25.6 mmol) and N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (8.54 g, 56.2 mmol). After stirring for 5-10 min. ammonium bicarbonate (15.3 g, 204 mmol) was added. The reaction mixture was stirred at room temperature for overnight. The solvent was then removed under reduced pressure and the residue was dissolved in aqueous sodium bicarbonate and dichloromethane. The aqueous phase was extracted with 9:1 dichloromethane:methanol. The organic layer was dried and evaporated. The residue was chromatographed on silica gel, eluting with 10-20% methanol/dichloromethane, to give the desired compound (4.15 g, 35%). Impure fractions were chromatographed again to give further product (1.02 g).

Workup

  1. additionwas added
  2. customThe solvent was then removed under reduced pressure
  3. dissolutionthe residue was dissolved in aqueous sodium bicarbonate
  4. extractionThe aqueous phase was extracted with 9:1 dichloromethane
  5. customThe organic layer was dried
  6. customevaporated
  7. customThe residue was chromatographed on silica gel
  8. washeluting with 10-20% methanol/dichloromethane

Sources & evidence

ORD record
ord-197c2d92777b4a248c3ab1b1c83dc793
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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