Water → HCID 17819198, compound

HRID 1988300Notes

Reaction equation

HRID 1988300 reaction equation
[NH:1]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:2]([C:11]([OH:13])=O)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.Cl.[CH3:49][NH:50][O:51][CH3:52].O>C(Cl)Cl>[C:17]([O:16][C:14](=[O:15])[NH:1][CH:2]([C:11](=[O:13])[N:50]([O:51][CH3:52])[CH3:49])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([F:10])=[CH:8][CH:9]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 7020910N-(tert-Butoxycarbonyl)-4-fluoro-L-phenylalanine

Product 1

HCID 17819198HCID 17819198, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Boc-Phe(4-F)-OH (5.0 g, 17.7 mmol) in methylene chloride (89 ml), BOP reagent (9.39 g, 21.2 mmol), N,O-dimethylhydroxylamine hydrochloride (2.07 g, 21.2 mmol) and TEA (5.92 ml, 42.5 mmol) were added under cooling with ice and stirred for 30 min. The reaction mixture was mixed with water and extracted with methylene chloride. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated to remove the solvent under reduced pressure. The thus obtained residue was subjected to silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:1), giving the titled compound (5.76 g, 100%).

Workup

  1. temperatureunder cooling with ice
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customto remove the solvent under reduced pressure

Sources & evidence

ORD record
ord-aefc74123bd1477981633000ee0f4a67
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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