Ethanol → HCID 20648927, compound

HRID 325247Notes

Reaction equation

HRID 325247 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH:15]([CH2:16][O:17][CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[CH2:14][CH2:13][O:12]2)=[CH:6][C:5]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH3:30].[OH-].[Na+].C(O)C.P(=O)(O)(O)O>O>[CH:18]1([O:17][CH2:16][CH:15]2[CH2:14][CH2:13][O:12][N:11]2[CH2:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:31])=[O:2])=[C:5]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[CH3:30])[CH:6]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 702EthanolHCID 1004Phosphoric AcidHCID 14798Sodium HydroxideHCID 20649182HCID 20649182, compound

Product 1

HCID 20648927HCID 20648927, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of example 1130C (355 mg, 0.84 mmol) and sodium hydroxide (1 mL of a 4N aqueous solution, 4 mmol) in 4 mnL of ethanol was heated to reflux for 6 hours and then cooled to room temperature. The mixture was diluted with water and the pH adjusted to 5 with aqueuos phosphoric acid. The mixture was extracted with 3 portions of ethyl acetate and the combined organic fractions were washed with water and brine, dried, filtered and concentrated to provide 270 mg (78%) of the title compound. MS (ESI+): 410 (MH+).

Workup

  1. temperatureto reflux for 6 hours
  2. extractionThe mixture was extracted with 3 portions of ethyl acetate
  3. washthe combined organic fractions were washed with water and brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-05268e5fe38f478896ab3efe9ff3e6d6
Source dataset
uspto-grants-2001_04
Patent number
US06221865B1

Reaction notes

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