Triethylamine → HCID 131722214, compound

HRID 1275169Notes

Reaction equation

HRID 1275169 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12]([OH:14])=O)[CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.[ClH:26].ON1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2N=N1.C(N(CC)CC)C.[ClH:44].ClC1C=C([N:53]2[CH2:58][CH2:57][O:56][C@H:55]([CH2:59][CH2:60][OH:61])[CH2:54]2)C=CC=1Cl.[Cl-].[NH4+]>C(Cl)Cl.O>[Cl:26][C:32]1[CH:33]=[C:34]([CH:54]2[C@@H:55]([CH2:59][CH2:60][OH:61])[O:56][CH2:57][CH2:58][N:53]2[C:12](=[O:14])[CH2:11][C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([O:4][CH:1]([CH3:2])[CH3:3])[CH:6]=2)[CH:35]=[CH:36][C:31]=1[Cl:44]

Participants

9

Reactant 6

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 166389242-(3-(Propan-2-yloxy)phenyl)acetic acidHCID 69954870HCID 69954870, compound

Product 1

HCID 131722214HCID 131722214, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1.03 g (5.28 mmole) of 3-isopropoxyphenylacetic acid were dissolved in 50 ml of methylene chloride, and 1.10 g (5.76 mmole) of WSC.HCl (Water Soluble Carbodiimide.HCl), 780 mg (5.76 mmole) of 1-hydroxybenzotriazol.H2O, 1.61 ml (11.5 mmole) of triethylamine, and 1.50 g (4.80 mmole) of (2R)-(3,4-dichlorophenyl)-2-(2-hydroxyethyl)morpholine hydrochloride [prepared as described in Example 76(c)] were added to the resulting solution, in that order. The mixture was then stirred at room temperature for 15 hours under a nitrogen atmosphere. At the end of this time, a saturated aqueous solution of ammonium chloride was added to the reaction mixture, which was then extracted with ethyl acetate. The organic extract was washed with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography, using a gradient elution method, with mixtures of hexane and ethyl acetate ranging from 3:1 to 2:1 by volume as the eluent, to give 1.81 g of the title compound.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order
  4. dry with materialafter which it was dried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography
  7. washa gradient elution method

Sources & evidence

ORD record
ord-9d0bf27425af4fe88b4752e18b688ddf
Source dataset
uspto-grants-2000_12
Patent number
US06159967

Reaction notes

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