Pyridine → HCID 57947471, compound

HRID 340970Notes

Reaction equation

HRID 340970 reaction equation
[C:1]([O:5][C:6]([N:8](C)[C@H:9]([CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH2:10][CH2:11][C:12](OC)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[C:32](Cl)(=[O:34])[CH3:33].C1C[O:39]CC1>>[C:32]([O:34][CH2:12][CH2:11][CH2:10][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:16][O:17][Si:18]([C:21]([CH3:22])([CH3:23])[CH3:24])([CH3:19])[CH3:20])(=[O:39])[CH3:33]

Participants

5

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 57947505HCID 57947505, compound

Product 1

HCID 57947471HCID 57947471, compoundYield 95%

Procedure

To a solution of (S)-methyl 4-(tert-butoxycarbonyl(methyl)amino)-5-(tert-butyldimethylsilyloxy)pentanoate (111 mmol) and pyridine (150 mL, 1.662 mol) in THF (500 mL) was added acetyl chloride (150 mL, 333.2 mmol) at 0° C. The resulting mixture was stirred at RT for 1 h. The solvent was removed and the remaining residue was diluted with EtOAc. The organic mixture was washed with water and brine, dried over Na2SO4, filtered, and concentrated. The residue was purified on silica gel column to give (S)-4-(tert-butoxycarbonylamino)-5-(tert-butyldimethylsilyloxy)pentyl acetate (39.6 g, 95%). LRMS (M+H+-Boc) m/z 276.2.

Workup

  1. customThe solvent was removed
  2. additionthe remaining residue was diluted with EtOAc
  3. washThe organic mixture was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on silica gel column

Sources & evidence

ORD record
ord-60b893b4c2db4960a33fae1b11ed9858
Source dataset
uspto-grants-2014_11
Patent number
US08895582B2

Reaction notes

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