Triethylamine → HCID 10097578, compound

HRID 1859865Notes

Reaction equation

HRID 1859865 reaction equation
[CH2:1]([N:3](CC)[CH2:4]C)C.Cl.CNC.[CH2:12]([CH:16]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][NH:30][C:31]([C:33]2[CH:38]=[CH:37][C:36]([C:39]3[CH:44]=[CH:43][C:42]([CH:45]=O)=[CH:41][CH:40]=3)=[CH:35][CH:34]=2)=[O:32])=[CH:23][CH:22]=1)[C:17]([OH:19])=[O:18])[CH2:13][CH2:14][CH3:15].[BH4-].[Na+]>C(O)C.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].C(O)(=O)C>[CH2:12]([CH:16]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][NH:30][C:31]([C:33]2[CH:38]=[CH:37][C:36]([C:39]3[CH:44]=[CH:43][C:42]([CH2:45][N:3]([CH3:4])[CH3:1])=[CH:41][CH:40]=3)=[CH:35][CH:34]=2)=[O:32])=[CH:23][CH:22]=1)[C:17]([OH:19])=[O:18])[CH2:13][CH2:14][CH3:15]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 4311764Sodium borohydrideHCID 10434997HCID 10434997, compound

Product 1

HCID 10097578HCID 10097578, compound

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To triethylamine (0.56 ml), dimethylamine hydrochloride (167 mg) and titanium tetraisopropoxide (0.59 ml) was added a suspension of 2-butyl-3-[4-[2-(4′-formylbiphenyl-4-carbonylamino)ethoxy]phenyl]propionic acid (474 mg) in ethanol (20 ml) at ambient temperature to afford a clear solution. Sodium borohydride (60 mg) was added to the solution and the mixture was stirred under nitrogen atmosphere for 18 hours. At the end of this time 50% acetic acid was added to the reaction mixture. This mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The ethyl acetate layer was separated and washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. Diisopropyl ether was added to the residue to give the title compound (135 mg) as colorless crystals.

Workup

  1. customto afford a clear solution
  2. concentrationThis mixture was concentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and water
  4. customThe ethyl acetate layer was separated
  5. washwashed with saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. additionDiisopropyl ether was added to the residue

Sources & evidence

ORD record
ord-f6f062780d7c4f0a8b2ea8bf031c7a9a
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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