Ethyl Acetate → HCID 77230165, compound

HRID 1715259Notes

Reaction equation

HRID 1715259 reaction equation
[NH2:1]/[C:2](=[N:13]\[O:14][C:15](=O)[C:16]([CH3:19])([CH3:18])[CH3:17])/[CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOC(C)=O>C1COCC1>[C:16]([C:15]1[O:14][N:13]=[C:2]([CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[N:1]=1)([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 140526496HCID 140526496, compound

Product 1

HCID 77230165HCID 77230165, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of tert-butyl ((3Z)-3-amino-3-{[(2,2-dimethylpropanoyl)oxy]imino}propyl)carbamate, obtained in step II as describe above (51 g; 177 mmol; 1 eq.), in dry THF (1000 ml) under N2, is added dropwise at RT a solution of tetrabutylammonium fluoride solution (177.5 ml; 1 M; 177.5 mmol; 1 eq.) in dry THF (400 ml). At the end of addition, the initial white suspension becomes a yellow solution. The reaction is followed by NMR. After 2 h the reaction is complete. The reaction mixture is poured into EtOAc (1 l) and is washed with water (3×700 ml) and brine (3×700 ml). The organic layer is dried over MgSO4, filtered off and evaporated, affording the title compound as a beige solid (46.6 g, 98%).

Workup

  1. customobtained in step II
  2. additionAt the end of addition
  3. washis washed with water (3×700 ml) and brine (3×700 ml)
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered off
  6. customevaporated

Sources & evidence

ORD record
ord-f9ac00e2e6ca4e97a60cf5c55a9b7620
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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