Ethyl Acetate → HCID 18317857, compound

HRID 1700377Notes

Reaction equation

HRID 1700377 reaction equation
[C:1]([O:8]C([O-])=O)(=O)[O:2][C:3]([CH3:6])([CH3:5])[CH3:4].[CH3:12][C:13]1[CH:14]=[C:15]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21]1[CH:20]([C:26]3([C:30]([OH:32])=[O:31])[CH2:29][CH2:28][CH2:27]3)[NH:19][CH2:18][CH2:17][C:16]2=1.C(OCC)(=O)C.OS([O-])(=O)=O.[K+]>O1CCOCC1.[OH-].[Na+].O>[C:3]([O:2][C:1]([N:19]1[CH2:18][CH2:17][C:16]2[C:15]3[C:23](=[CH:24][CH:25]=[C:13]([CH3:12])[CH:14]=3)[NH:22][C:21]=2[CH:20]1[C:26]1([C:30]([OH:32])=[O:31])[CH2:29][CH2:28][CH2:27]1)=[O:8])([CH3:4])([CH3:5])[CH3:6]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 516920Potassium bisulfateHCID 18317894HCID 18317894, compoundHCID 22064466Tert-butyldicarbonate

Product 1

HCID 18317857HCID 18317857, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

5.52 g of tert-butyl pyrocarbonate are added to a solution of 6.5 g of the compound obtained in Example 37 in 50 ml of dioxane and 25 ml of 1M sodium hydroxide solution. After reaction for 20 hours at ambient temperature, 50 ml of ethyl acetate and 100 ml of water are added, and then the reaction mixture is acidified to pH 2.3 using a solution of KHSO4. The precipitate formed is filtered off, washed with water and dried, enabling the expected product to be isolated.

Workup

  1. customAfter reaction for 20 hours at ambient temperature
  2. customThe precipitate formed
  3. filtrationis filtered off
  4. washwashed with water
  5. customdried
  6. customto be isolated

Sources & evidence

ORD record
ord-c704bc9a21e547158ab5e7913b55f424
Source dataset
uspto-grants-2002_02
Patent number
US06350757B1

Reaction notes

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