Acetic Acid → HCID 178418570, compound

HRID 1870928Notes

Reaction equation

HRID 1870928 reaction equation
[NH2:1][C:2]1[C:3]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26](=[NH:34])[NH:27][O:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:16][CH:15]=2)=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH2:35]([O:37][C:38](OCC)(OCC)OCC)[CH3:36].C(O)(=O)C>O1CCOCC1>[CH2:35]([O:37][C:38]1[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26](=[NH:34])[NH:27][O:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:16][CH:15]=2)[C:3]2[C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:9][CH:10]=[CH:11][C:2]=2[N:1]=1)[CH3:36]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 66213Tetraethyl orthocarbonateHCID 178418614HCID 178418614, compound

Product 1

HCID 178418570HCID 178418570, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

The pale brown syrup (8.58 g) obtained in Example (57a) was dissolved in dioxane (20 ml). To the solution were added tetraethoxymethane (8.64 g) and acetic acid (1.56 g). The mixture was stirred for 2 hours at 100° C. The reaction mixture was concentrated to dryness. The residue was crystallized from ethyl acetate (50 ml). Resulting crystalline precipitates were collected by filtration to obtain the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customThe residue was crystallized from ethyl acetate (50 ml)
  3. customResulting crystalline precipitates
  4. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-e323f6e07f694e7cb6e264bdb10a85be
Source dataset
uspto-grants-2000_08
Patent number
US06100252

Reaction notes

Loading…