Pyridine → HCID 67234851, compound

HRID 1748277Notes

Reaction equation

HRID 1748277 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.C(OCC)(=O)C>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 86316722HCID 86316722, compound

Product 1

HCID 67234851HCID 67234851, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent2×

Procedure

To a stirred solution of thionyl chloride (2.9 g, 24.3 mmol) in acetonitrile (15 mL) is cooled to −45° C. is added a solution of tert-butyl [(3R)-3-hydroxybutyl]carbamate (1.8 g, 9.7 mmol) in acetonitrile (20 mL) by syringe over 10 min, keeping the internal temperature below −40° C. 4-Dimethylaminopyridine (119 mg, 0.97 mmol) is added followed by the slow addition of pyridine (3.9 mL, 48.6 mmol), keeping the temperature below −40° C. Ethyl acetate (50 mL) is added to the suspension and the mixture at −35° C. is filtered. The solid is washed with EtOAc and the filtrates are combined. Saturated Na2HPO4 solution (20 mL) is added into the filtrates and the mixture is stirred vigorously for 30 min. The organic layer is separated, washed with 1M NaHSO4, dried (MgSO4) and concentrated to afford the title compound (2.3 g, 99%) which is used in the next step without purification.

Workup

  1. customthe internal temperature below −40° C
  2. customthe temperature below −40° C
  3. filtrationthe mixture at −35° C. is filtered
  4. washThe solid is washed with EtOAc
  5. additionSaturated Na2HPO4 solution (20 mL) is added into the filtrates
  6. customThe organic layer is separated
  7. washwashed with 1M NaHSO4
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-dae5f5091c1e4d5d9bb31ba218bf3ac8
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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