Pyridine → HCID 67235126, compound

HRID 1748272Notes

Reaction equation

HRID 1748272 reaction equation
[S:1](Cl)(Cl)=[O:2].[OH:5][C@@H:6]([CH3:17])[CH2:7][CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13].N1C=CC=CC=1.CCOC(C)=O>C(#N)C.CN(C)C1C=CN=CC=1>[CH3:17][C@@H:6]1[O:5][S:1](=[O:2])[N:9]([C:10]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:16])[CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 86309633HCID 86309633, compound

Product 1

HCID 67235126HCID 67235126, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent2×

Procedure

To a solution of thionyl chloride (192 mL, 2.6 mol) in acetonitrile (1.0 L) at −40° C. is added dropwise a solution of tert-butyl [(3S)-3-hydroxybutyl]carbamate (200 g, 1.1 mol) in acetonitrile (2.5 L). The mixture is stirred for 10 min and 4-dimethylaminopyridine (12.9 g, 105.66 mmol) is added. After stirring for another 10 min, pyridine (427 mL, 5.3 mol) is added over 90 min, keeping the temperature below −40° C. EtOAc is added at −40° C. and the suspension is filtered to remove the solid. To the filtrate is added saturated Na2HPO4 solution and the mixture is stirred vigorously for 30 minutes at room temperature. The organic layer is separated, washed with 1M NaHSO4 solution, dried (Na2SO4) and concentrated to afford the title crude compound (250 g) as an oil which is used in the next step without purification.

Workup

  1. stirringAfter stirring for another 10 min
  2. customthe temperature below −40° C
  3. filtrationthe suspension is filtered
  4. customto remove the solid
  5. additionTo the filtrate is added saturated Na2HPO4 solution
  6. stirringthe mixture is stirred vigorously for 30 minutes at room temperature
  7. customThe organic layer is separated
  8. washwashed with 1M NaHSO4 solution
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-e33bfad3625549f2b283a9a83a0a2e89
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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