Cyanuric fluoride → HCID 14824297, compound

HRID 2055651Notes

Reaction equation

HRID 2055651 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-a48f5cd0341f4ca68f9f1edef6f179e0
Source dataset
uspto-grants-2008_02
Patent number
US07332498B2

Reaction notes

Loading…