Acetic Anhydride → HCID 69471805, compound

HRID 1294576Notes

Reaction equation

HRID 1294576 reaction equation
[CH3:1][C:2]1([CH3:27])[CH:7]2[CH2:8][CH:3]1[CH2:4][CH2:5][CH:6]2[CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][C:14]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)([C:17]#[N:18])[CH2:13][CH2:12]1.C(OC(=O)C)(=[O:30])C.[OH-].[Na+]>C(O)=O>[CH3:1][C:2]1([CH3:27])[CH:7]2[CH2:8][CH:3]1[CH2:4][CH2:5][CH:6]2[CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][C:14]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)([C:17]([NH2:18])=[O:30])[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 69476210HCID 69476210, compound

Product 1

HCID 69471805HCID 69471805, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 28.7 g (78 mmol) (28a), 135 ml of formic acid and 135 ml of acetic anhydride was stirred at room temperature for 1 day. The reaction was monitored by 1H-NMR and MS. After completed reaction the reaction mixture was poured into ice-water (800 ml). The pH was adjusted to 10 by the addition of 33% NaOH (aq). The aqueous layer was extracted with DCM (3×1 l). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in 550 ml tert.-butylalcohol, 45 ml water and 45 ml concentrated aqueous ammonia. The 90 ml of 35% hydrogen peroxide were added drop wise at room temperature. The mixture was stirred overnight. The reaction was monitored by TLC. 900 ml of water were added and the mixture was extracted with DCM (3×500 ml). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to give 29.3 g (76 mmol, 98%) of (29a) as a yellow solid, which was used in the next step without purification.

Workup

  1. customreaction the reaction mixture
  2. extractionThe aqueous layer was extracted with DCM (3×1 l)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in 550 ml tert.-butylalcohol
  6. additionThe 90 ml of 35% hydrogen peroxide were added drop wise at room temperature
  7. stirringThe mixture was stirred overnight
  8. addition900 ml of water were added
  9. extractionthe mixture was extracted with DCM (3×500 ml)
  10. dry with materialThe combined organic layers were dried over Na2SO4
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e192b35a313e4b78a9f46b64f7098856
Source dataset
uspto-grants-2007_07
Patent number
US07241770B2

Reaction notes

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