Acetic Acid → HCID 59331506, compound

HRID 1882100Notes

Reaction equation

HRID 1882100 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10](/[C:13](=[CH:32]\[CH:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)/[C:14](=O)[CH2:15][CH2:16][C:17]([C:19]3[CH:24]=[CH:23][C:22]([CH:25]([OH:30])[C:26]([OH:29])([CH3:28])[CH3:27])=[CH:21][N:20]=3)=O)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.C([O-])(=O)C.[NH4+:43].C(O)(=O)C.[OH-].[Na+]>O>[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10](/[C:13](/[C:14]3[NH:43][C:17]([C:19]4[N:20]=[CH:21][C:22]([CH:25]([OH:30])[C:26]([CH3:27])([OH:29])[CH3:28])=[CH:23][CH:24]=4)=[CH:16][CH:15]=3)=[CH:32]\[CH:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 517165Ammonium AcetateHCID 59331428HCID 59331428, compound

Product 1

HCID 59331506HCID 59331506, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (5E)-5-[4-(cyclopropylsulfonyl)phenyl]-1-[5-(1,2-dihydroxy-2-methylpropyl)pyridin-2-yl]-6-(tetrahydro-2H-pyran-4-yl)hex-5-ene-1,4-dione (4.79 g), ammonium acetate (3.40 g) and acetic acid (15 mL) was stirred at 90° C. for 2 hr. Water was added to the reaction mixture, and the mixture was neutralized with 8N aqueous sodium hydroxide solution. The precipitated solid was collected by filtration, washed with water, and dried. The obtained solid was dissolved in tetrahydrofuran, and the solution was treated with activated carbon and concentrated. Cold ethyl acetate was added to the obtained residue to allow crystallization. The crystals were collected by filtration, washed with cold ethyl acetate and dried to give the title compound (3.38 g, yield 73%) as pale-yellow crystals. melting point 196-197° C. MS: 523 (MH+).

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. washwashed with water
  3. customdried
  4. dissolutionThe obtained solid was dissolved in tetrahydrofuran
  5. additionthe solution was treated with activated carbon
  6. concentrationconcentrated
  7. additionCold ethyl acetate was added to the obtained residue
  8. customcrystallization
  9. filtrationThe crystals were collected by filtration
  10. washwashed with cold ethyl acetate
  11. customdried

Sources & evidence

ORD record
ord-d5f9aa1036f847a3bc3a0a3c0cd5aff9
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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