Acetic Acid → HCID 44129296, compound

HRID 1514292Notes

Reaction equation

HRID 1514292 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:35]=[CH:34][C:20]4[CH2:21][CH2:22][N:23]([CH2:26][CH2:27][CH2:28][C:29]([O:31]CC)=[O:30])[CH2:24][CH2:25][C:19]=4[CH:18]=3)[N:13]=2)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[OH-].[Na+].C(O)(=O)C>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:35]=[CH:34][C:20]4[CH2:21][CH2:22][N:23]([CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])[CH2:24][CH2:25][C:19]=4[CH:18]=3)[N:13]=2)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 59403439HCID 59403439, compound

Product 1

HCID 44129296HCID 44129296, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
50 °C

Procedure

A suspension of ethyl 4-[7-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]butanoate (Preparation 97) (185 mg, 0.371 mmol) in ethanol (3 ml), was treated with 2M sodium hydroxide (0.556 ml, 1.11 mmol) at room temperature overnight to give a colourless precipitate. A further 1-2 mls of ethanol was added and the temperature was raised to 50° C. to complete the reaction. Acetic acid (0.07 ml, 1.22 mmol) was added to the solution and the mixture concentrated. The resultant oily residue was treated with water (ca 3 ml) then stirred at room temperature for 1-2 hr and filtered. The solid was washed with water, then dissolved in methanol and the solvent evaporated. The resultant solid was dried overnight in vacuo at ca 60° C. to give the title compound (153 mgs).

Workup

  1. customto give a colourless precipitate
  2. customthe reaction
  3. concentrationthe mixture concentrated
  4. additionThe resultant oily residue was treated with water (ca 3 ml)
  5. filtrationfiltered
  6. washThe solid was washed with water
  7. dissolutiondissolved in methanol
  8. customthe solvent evaporated
  9. customThe resultant solid was dried overnight in vacuo at ca 60° C.

Sources & evidence

ORD record
ord-9e17aaa80916432693e2422cc627379e
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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