Hydrochloric Acid → HCID 86682902, compound

HRID 1522878Notes

Reaction equation

HRID 1522878 reaction equation
[Si]([O:8][CH2:9][C@@H:10]([N:12]1[CH:16]=[C:15]([CH3:17])[N:14]=[CH:13]1)[CH3:11])(C(C)(C)C)(C)C.Cl>C(Cl)Cl.CCOCC>[CH3:17][C:15]1[N:14]=[CH:13][N:12]([C@@H:10]([CH3:11])[CH2:9][OH:8])[CH:16]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86682901HCID 86682901, compound

Product 1

HCID 86682902HCID 86682902, compoundYield 90.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution (S)-1-(1-((tert-butyldimethylsilyl)oxy)propan-2-yl)-4-methyl-1H-imidazole (0.425 g, 1.67 mmol) in DCM (5 mL) was added 3M HCl in ether (10 mL) at room temperature. The resulting mixture was stirred at room temperature overnight. The mixture was concentrated under vacuum. The residue was dissolved in MeOH, and solid NaHCO3 was added. The mixture was stirred at room temperature for 1 h. The solid was filtered and washed with MeOH. The combined organic layers were concentrated to afford the title compound (0.212 g). 1H NMR (CDCl3): δ 7.33 (s, 1H), 6.63 (s, 1H), 4.18-4.12 (m, 1H), 3.78-3.47 (m, 2H), 2.10 (s, 3H), 1.42 (d, 3H); LCMS: 141 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. dissolutionThe residue was dissolved in MeOH
  3. additionsolid NaHCO3 was added
  4. stirringThe mixture was stirred at room temperature for 1 h
  5. filtrationThe solid was filtered
  6. washwashed with MeOH
  7. concentrationThe combined organic layers were concentrated

Sources & evidence

ORD record
ord-5c3e744ecffe4ebf94ea3b0e8b00be94
Source dataset
uspto-grants-2015_07
Patent number
US09078871B2

Reaction notes

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