Acetic Anhydride → HCID 20613752, compound

HRID 1840889Notes

Reaction equation

HRID 1840889 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[N:8]12[CH2:15][CH2:14][CH:11]([CH2:12][CH2:13]1)[C@@H:10]([NH:16][C:17](=[O:27])/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[NH2:26])[CH2:9]2.C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])[O-]>C(O)=O>[N:8]12[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15]1)[C@@H:10]([NH:16][C:17](=[O:27])/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[NH:26][CH:1]=[O:3])[CH2:9]2

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 19660Carbonate IonHCID 20613751HCID 20613751, compound

Product 1

HCID 20613752HCID 20613752, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Formic acid (98%, 2.9 mL) and acetic anhydride (1.0 mL) were combined under an inert atmosphere while cooling with a cold water bath. (R)-N-(1-Azabicyclo[2.2.2]oct-3-yl)(E-3-(2-aminophenyl)propenamide) (0.16 g, 0.00059 moles) was added and the reaction was stirred for three days at room temperature. The solution was poured into saturated sodium carbonate and more solid carbonate was added until the solution was basic. The aqueous layer was extracted four times with chloroform. The organic extracts were combined, dried (MgSO4), and concentrated in vacuo. The product was transferred using chloroform and this was stripped and chased with two portions of ether. The white solid was dried at room temperature with high vacuum, giving 64 mg; MS (ES+) 300 (MH+).

Workup

  1. temperaturewhile cooling with a cold water bath
  2. additionwas added until the solution
  3. extractionThe aqueous layer was extracted four times with chloroform
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe white solid was dried at room temperature with high vacuum
  7. customgiving 64 mg

Sources & evidence

ORD record
ord-6631348781b24a70bcf6cbbf2b4a56bd
Source dataset
uspto-grants-2004_01
Patent number
US06683090B1

Reaction notes

Loading…