Pyridine → HCID 67235477, compound

HRID 1748285Notes

Reaction equation

HRID 1748285 reaction equation
[S:1](Cl)(Cl)=[O:2].[OH:5][CH:6]([CH3:18])[CH:7]([CH3:17])[CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13].N1C=CC=CC=1.C(OCC)(=O)C>C(#N)C.CN(C)C1C=CN=CC=1>[CH3:17][CH:7]1[CH:6]([CH3:18])[O:5][S:1](=[O:2])[N:9]([C:10]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:16])[CH2:8]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 45092006HCID 45092006, compound

Product 1

HCID 67235477HCID 67235477, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent2×

Procedure

To a stirred solution of thionyl chloride (5.4 g, 45.4 mmol) in acetonitrile (25 mL) cooled to −45° C. is added a solution of tert-butyl (3-hydroxy-2-methylbutyl)carbamate (3.7 g, 18.1 mmol) in acetonitrile (35 mL) by syringe over about 15 min, keeping the internal temperature below −40° C. When the addition is completed, solid 4-dimethylamino pyridine (222 mg, 1.8 mmol) is added in one portion followed by pyridine (7.3 mL, 90.8 mmol), keeping the temperature below −40° C. The mixture is stirred at −40° C. to −35° C. for 1 h. Ethyl acetate (100 mL) is added and the mixture is filtered at −35° C. The solid is washed with EtOAc and discarded. To the filtrate is added saturated Na2HPO4 solution (20 mL) and the mixture is stirred vigorously for 3 h. The organic layer is separated, washed with 1M NaHSO4, dried (MgSO4) and concentrated to afford the title compound (4.4 g) which is used in the next step without purification.

Workup

  1. customthe internal temperature below −40° C
  2. additionWhen the addition
  3. customthe temperature below −40° C
  4. filtrationthe mixture is filtered at −35° C
  5. washThe solid is washed with EtOAc
  6. additionTo the filtrate is added saturated Na2HPO4 solution (20 mL)
  7. stirringthe mixture is stirred vigorously for 3 h
  8. customThe organic layer is separated
  9. washwashed with 1M NaHSO4
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-9205c565dd22433a84645de685a813df
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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