Hydrochloric Acid → HCID 89408386, compound

HRID 516212Notes

Reaction equation

HRID 516212 reaction equation
[C:1]([O:5][C:6](=[O:21])[N:7]([C@H:9]([C:13]1[C:18]([F:19])=[C:17]([Cl:20])[CH:16]=[CH:15][N:14]=1)[CH2:10][CH:11]=C)[CH3:8])([CH3:4])([CH3:3])[CH3:2].Cl.CCN(C(C)C)C(C)C.[O:32](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O>O1CCOCC1.CO>[Cl:20][C:17]1[CH:16]=[CH:15][N:14]=[C:13]([C@@H:9]([N:7]([CH3:8])[C:6](=[O:21])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:10][CH:11]=[O:32])[C:18]=1[F:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 90495Di-tert-butyl dicarbonateHCID 117901401HCID 117901401, compound

Product 1

HCID 89408386HCID 89408386, compoundYield 101%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

(S)-tert-Butyl(1-(4-chloro-3-fluoropyridin-2-yl)but-3-en-1-yl)(methyl)carbamate: A solution of Intermediate 30A (0.11 g, 0.345 mmol), 4 N HCl in dioxane (3 mL), and MeOH (3.00 mL) was stirred at rt for 1 h. The reaction mixture was concentrated. The residue was re-dissolved in acetonitrile (3.00 mL) and added DIEA (0.241 mL, 1.380 mmol) followed by BOC2O (0.104 mL, 0.449 mmol). The reaction was stirred at rt for 2 h and concentrated. The residue was purified by silica gel chromatography to yield the desired product (0.11 g, 101%). MS (ESI) m/z: 314.9 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionThe residue was re-dissolved in acetonitrile (3.00 mL)
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-e47c7e977d5f43e4830192783c527378
Source dataset
uspto-grants-2015_08
Patent number
US09108981B2

Reaction notes

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