HCID 57947701, compound → HCID 57947421, compound

HRID 340974Notes

Reaction equation

HRID 340974 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([NH:15][CH3:16])[CH2:11][CH2:12][CH2:13][OH:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[F:17][C:18]1[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:19]=1[CH2:20][NH:21][C:22](=[O:33])OC1C=CC([N+]([O-])=O)=CC=1>C1COCC1>[Si:1]([O:8][CH2:9][C@@H:10]([N:15]([CH3:16])[C:22]([NH:21][CH2:20][C:19]1[CH:34]=[CH:35][CH:36]=[C:37]([F:38])[C:18]=1[F:17])=[O:33])[CH2:11][CH2:12][CH2:13][OH:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 57947701HCID 57947701, compoundHCID 57947736HCID 57947736, compound

Product 1

HCID 57947421HCID 57947421, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-5-(tert-butyldimethylsilyloxy)-4-(methylamino)pentan-1-ol (109.2 mmol) in THF (200 mL) was added 4-nitrophenyl 2,3-difluorobenzylcarbamate (43.72 g, 142.0 mmol). The resulting solution was stirred at RT for 1 h. The solvent was removed and the resulting residue was dissolved in EtOAc (800 mL). The organic mixture was washed with NaOH (1 N, 100 mL×3), HCl (0.5 N, 100 mL), NaHCO3 (sat.), and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified on silica gel column using a mixture of EtOAC and hexanes to give (S)-1-(1-(tert-butyldimethylsilyloxy)-5-hydroxypentan-2-yl)-3-(2,3-difluorobenzyl)-1-methylurea (35.1 g, 76%) as a pale yellow oil. LRMS (M+H+) m/z 417.2.

Workup

  1. customThe solvent was removed
  2. dissolutionthe resulting residue was dissolved in EtOAc (800 mL)
  3. washThe organic mixture was washed with NaOH (1 N, 100 mL×3), HCl (0.5 N, 100 mL), NaHCO3 (sat.), and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified on silica gel column
  8. additiona mixture of EtOAC and hexanes

Sources & evidence

ORD record
ord-955fd1b700f44f5293e074ffbf4f90f4
Source dataset
uspto-grants-2014_11
Patent number
US08895582B2

Reaction notes

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