Tetrabutylammonium Fluoride → HCID 58868931, compound

HRID 1441969Notes

Reaction equation

HRID 1441969 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([O:23][C:24]([NH:26][C@H:27]([C:46]([O:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:47])[CH2:28][C:29]1[C:34]([N+:35]([O-:37])=[O:36])=[CH:33][CH:32]=[C:31]([O:38][Si](C(C)(C)C)(C)C)[CH:30]=1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>C1COCC1>[C:19]([O:23][C:24]([NH:26][C@H:27]([C:46]([O:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:47])[CH2:28][C:29]1[C:34]([N+:35]([O-:37])=[O:36])=[CH:33][CH:32]=[C:31]([OH:38])[CH:30]=1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58868985HCID 58868985, compound

Product 1

HCID 58868931HCID 58868931, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

10.4 ml (10.4 mmol) of a 1N tetrabutylammonium fluoride solution in THF are added to a solution of 2.77 g (5.22 mmol) of benzyl N-(tert-butoxycarbonyl)-3-{[tert-butyl(dimethyl)silyl]oxy}-6-nitro-L-phenylalaninate (Example 5I) in 50 ml of THF, and the mixture is stirred at RT for 30 min. The solution is then poured into ice-water and extracted several times with ethyl acetate. The organic phase is dried over magnesium sulfate and concentrated in vacuo. The crude product is dried to constant weight under high vacuum.

Workup

  1. extractionextracted several times with ethyl acetate
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. dry with materialThe crude product is dried to constant weight under high vacuum

Sources & evidence

ORD record
ord-dc3ce04196dd4abbad5b5247f30ad7d4
Source dataset
uspto-grants-2010_02
Patent number
US07655643B2

Reaction notes

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