Acetic Anhydride → HCID 90093641, compound

HRID 1753082Notes

Reaction equation

HRID 1753082 reaction equation
[C:1](OC(=O)C)(=O)C.[CH:8]1([C:11]([NH:13][CH:14]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:15]([OH:17])=O)=[O:12])[CH2:10][CH2:9]1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[CH:8]1([C:11]([NH:13][CH:14]([C:15](=[O:17])[CH3:1])[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:12])[CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 90094053HCID 90094053, compound

Product 1

HCID 90093641HCID 90093641, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

DMAP (5 g, 0.041 mol) and acetic anhydride (306 g, 3 mol) were added to a suspension of 2-[(cyclopropylcarbonyl)amino]-4-ethoxy-4-oxobutanoic acid (Preparation 85, 229 g, 1 mol) in freshly-distilled pyridine (1.5 L). The reaction was heated at 90° C. for 2 hours before concentrating in vacuo at 60° C., azeotroping with toluene. The residue was purified by silica gel column chromatography eluting with 2% methanol in chloroform to afford the title compound (70%) that was taken directly on to the next step.

Workup

  1. concentrationbefore concentrating in vacuo at 60° C.
  2. customazeotroping with toluene
  3. customThe residue was purified by silica gel column chromatography
  4. washeluting with 2% methanol in chloroform

Sources & evidence

ORD record
ord-39f817ad84534e4abb5d86382a2851ad
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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