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Pyridine → t-Butoxycarbonylvaline fluoride

HRID 1941341
Notes
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Reaction equation

HRID 1941341 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]([OH:15])=O)[CH:10]([CH3:12])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.N1C(F)=NC(F)=NC=1[F:24]>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]([F:24])=[O:15])[CH:10]([CH3:12])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1049PyridineHCID 12664Cyanuric fluorideHCID 83693Boc-L-Valine

Product 1

HCID 10751345t-Butoxycarbonylvaline fluoride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-15 °C

Procedure

To a cooled (-15° C.) solution of t-butoxycarbonylvaline (1.0 g, 4.6 mmol) and pyridine (0.39 ml) in methylene chloride (11 ml) is dropped cyanuric fluoride (1.87 g, 13.8 mmol) and the mixture is stirred at -15° C. for 1 hour. The reaction mixture is diluted with methylene chloride and ice, and filtered on Celite. The filtrate is diluted with ice water and extracted with methylene chloride. The organic layer is dried over magnesium sulfate and concentrated in vacuo to give t-butoxycarbonylvaline fluoride.

Workup

  1. filtrationfiltered on Celite
  2. additionThe filtrate is diluted with ice water
  3. extractionextracted with methylene chloride
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c9c879df60e34e589be632a5a6c87015
Source dataset
uspto-grants-1997_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05703106

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes