Pyridine → HCID 11557505, compound

HRID 1486765Notes

Reaction equation

HRID 1486765 reaction equation
[OH:1][C@@H:2]([CH3:6])[C:3]([NH2:5])=[O:4].[C:7]([Si:11]([CH3:14])([CH3:13])Cl)([CH3:10])([CH3:9])[CH3:8].N1C=CC=CC=1>CN(C=O)C>[Si:11]([O:1][C@@H:2]([CH3:6])[C:3]([NH2:5])=[O:4])([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 28928tert-Butyldimethylsilyl chlorideHCID 1530235(S)-(-)-Lactamide

Product 1

HCID 11557505HCID 11557505, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (S)-2-hydroxypropanamide (13-1) (30 g, 337 mmol) and tert-butyldimethylchlorosilane (66.0 g, 438 mmol) in pyridine (101 ml, 1246 mmol) and DMF (90 ml) was stirred at room temperature for 16 h. The reaction mixture was filtered to remove insolubles and the filtrate was partitioned between saturated aqueous sodium bicarbonate solution (500 mL) and EtOAc (500 mL). The organic layer was washed with saturated aqueous sodium bicarbonate solution (2×100 mL), brine (3×100 mL) and water (3×100 mL). The organic layer was dried over sodium sulfate, filtered and concentrated to afford 13-2 as a viscous yellow oil. MS: m/z=204.0 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove insolubles
  3. customthe filtrate was partitioned between saturated aqueous sodium bicarbonate solution (500 mL) and EtOAc (500 mL)
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution (2×100 mL), brine (3×100 mL) and water (3×100 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-282640e92ae244df849cc6007a8f2cd1
Source dataset
uspto-grants-2016_08
Patent number
US09428492B2

Reaction notes

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