Acetic Anhydride → HCID 117635545, compound

HRID 920220Notes

Reaction equation

HRID 920220 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2.[C:20](OC(=O)C)(=[O:22])[CH3:21]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:20]([O:1][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)(=[O:22])[CH3:21]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 59151432HCID 59151432, compound

Product 1

HCID 117635545HCID 117635545, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

In a 10 dram vial, added 1-7 (300 mg, 0.795 mmol) to pyridine (3975 μl) followed by acetic anhydride (225 μl, 2.385 mmol) and DMAP (9.71 mg, 0.080 mmol). After 1 h, LCMS showed complete consumption of R1 desired product. Partitioned between 10 mL H2O and 10 mL EtOAc, separated layers. Back-extracted aqueous with 1×5 mL EtOAc. Washed combined organics with 5×5 mL H2O. Dried combined organics over Na2SO4, filtered, concentrated to give a pale yellow oil. Purification by normal-phase HPLC (40 g ISCO column, 0-50% EtOAc:Hexanes) gave 7-1 as a clear, colorless oil.

Workup

  1. customconsumption of R1 desired product
  2. customPartitioned between 10 mL H2O and 10 mL EtOAc
  3. customseparated layers
  4. washWashed
  5. customDried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a pale yellow oil
  9. customPurification by normal-phase HPLC (40 g ISCO column, 0-50% EtOAc:Hexanes)
  10. customgave 7-1 as a clear, colorless oil

Sources & evidence

ORD record
ord-90bb506b52bd4ce9bf8434539c9515a4
Source dataset
uspto-grants-2016_03
Patent number
US09273040B2

Reaction notes

Loading…