Acetic Acid → HCID 18625751, compound

HRID 1859864Notes

Reaction equation

HRID 1859864 reaction equation
[BH4-].[Na+].[CH2:3]([CH:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][NH:21][C:22]([C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][C:33]([CH:36]=[O:37])=[CH:32][CH:31]=3)=[CH:26][CH:25]=2)=[O:23])=[CH:14][CH:13]=1)[C:8]([OH:10])=[O:9])[CH2:4][CH2:5][CH3:6].C(O)(=O)C>C(O)C>[CH2:3]([CH:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][NH:21][C:22]([C:24]2[CH:25]=[CH:26][C:27]([C:30]3[CH:31]=[CH:32][C:33]([CH2:36][OH:37])=[CH:34][CH:35]=3)=[CH:28][CH:29]=2)=[O:23])=[CH:14][CH:13]=1)[C:8]([OH:10])=[O:9])[CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 10434997HCID 10434997, compound

Product 1

HCID 18625751HCID 18625751, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (95%, 34 mg) was added to a solution of 2-butyl-3-[4-[2-(4′-formylbiphenyl-4-carbonylamino)ethoxy]phenyl]propionic acid (366 mg) in ethanol (10 ml) at ambient temperature. The mixture was stirred for 1.5 hours. At the end of this time 50% acetic acid was added to the reaction mixture. The 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 (331 mg) as colorless crystals.

Workup

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

Sources & evidence

ORD record
ord-786dca0dd36c48d892b5a31b760c66f0
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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