Acetic Acid → HCID 67434480, compound

HRID 1946547Notes

Reaction equation

HRID 1946547 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]([C:18](C([O-])=O)(C([O-])=O)[C:19]([O:21]C)=[O:20])[CH2:15][CH2:16][CH2:17][C:12]=3[N:11]=[C:10]2[CH:29]([CH3:31])[CH3:30])=[CH:4][CH:3]=1.[OH-].[Na+].C(O)(=O)C>C(O)C>[C:19]([OH:21])(=[O:20])[CH3:18].[I:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[C:13]3[CH:14]([CH2:18][C:19]([OH:21])=[O:20])[CH2:15][CH2:16][CH2:17][C:12]=3[N:11]=[C:10]2[CH:29]([CH3:31])[CH3:30])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 86658182HCID 86658182, compound

Product 1

HCID 67434480HCID 67434480, compoundYield 132.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of Intermediate 89 (11.1 g) in Ethanol (150 mL) was added 2M Aqueous Sodium Hydroxide (36.4 mL). The reaction mixture was then stirred at 80° C. and under nitrogen for 3 h. The reaction mixture was concentrated in vacuo, glacial acetic acid (41.6 mL, 727 mmol) added and allowed to stir at 120° C. and under nitrogen for 2 h. The reaction mixture was concentrated under vacuum. The white solid was suspended and stirred in ether (500 mL) for 5 mins. The white solid was filtered off under vacuum. The solid was suspended in EtOAc (500 mL) and the suspension was refluxed for 45 mins. The white solid was hot filtered under vacuum and washed with EtOAc (100 mL). The filtrate was concentrated under vacuum to give the title compound as a white solid (6.8 g). LC/MS MH+ 439, Rt 1.90 min (5 min run).

Workup

  1. additionadded
  2. stirringto stir at 120° C. and under nitrogen for 2 h
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. stirringstirred in ether (500 mL) for 5 mins
  5. filtrationThe white solid was filtered off under vacuum
  6. temperaturethe suspension was refluxed for 45 mins
  7. filtrationThe white solid was hot filtered under vacuum
  8. washwashed with EtOAc (100 mL)
  9. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-8ab00c1cc22741ae9a42c0c839f29a58
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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