Ethyl Acetate → HCID 19704254, compound

HRID 861545Notes

Reaction equation

HRID 861545 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]([S:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[C:8]([CH:10]([CH:12]=[CH2:13])[OH:11])[N:9]=1)[CH2:2][CH2:3][CH3:4].C(OCC)(=O)C>O1CCOCC1.O=[Mn]=O>[CH2:1]([C:5]1[NH:9][C:8]([C:10](=[O:11])[CH:12]=[CH2:13])=[C:7]([S:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 178458936HCID 178458936, compound

Product 1

HCID 19704254HCID 19704254, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

3 g of the product of Stage 3 were dissolved at 30° C. in 60 ml of dioxane and the medium was allowed to return to ambient temperature. 1.56 g (2 equivalents) of MnO2 were added about every 30 minutes for about 2 hours, that being 10 equivalents in total. The mixture was poured into 500 ml of ethyl acetate and filtration was carried out. The filtrate was evaporated to dryness to obtain 2.7 g of a yellow solid which was chromatographed on silica with AcOEt/flugene (1-2) to obtain 2.1 g of the expected product (vivid yellow solid).

Workup

  1. customto return to ambient temperature
  2. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-8dc26b61dff54c3485af10fc543c809a
Source dataset
uspto-grants-1998_02
Patent number
US05714508

Reaction notes

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