Cyanuric fluoride → HCID 14824297, compound

HRID 1823679Notes

Reaction equation

HRID 1823679 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:16]([OH:18])=O)[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C(F)=NC(F)=NC=1[F:21]>ClCCl>[CH2:1]([O:8][C:9](=[O:10])[NH:11][CH:12]([C:16]([F:21])=[O:18])[CH:13]([CH3:15])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12664Cyanuric fluorideHCID 712434N-alpha-Benzyloxycarbonyl-D-valine

Product 1

HCID 14824297HCID 14824297, compoundYield 120.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Formula 502 where R6 is Isopropyl and R6′ is H: To a solution of dichloromethane (100 mL) and N-benzyloxycarbonyl D-valine (9 g, 35.8 mmol) was added cyanuric fluoride (2.4 mL, 26.1 mmol). The reaction mixture was stirred overnight and then filtered through Celite. The remaining solution was washed with ice-water and dried over sodium sulfate. The solvent was evaporated under reduced pressure to give the substantially pure acid fluoride product of Formula 502, (1-fluorocarbonyl-2-methyl-propyl)-carbamic acid benzyl ester (7.94 g, 87.6%).

Workup

  1. filtrationfiltered through Celite
  2. washThe remaining solution was washed with ice-water
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-59af9348f4f04857a4054bf42c8b266e
Source dataset
uspto-grants-2006_05
Patent number
US07038048B2

Reaction notes

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