Hydrochloric Acid → Hydrochloric Acid

HRID 1424145Notes

Reaction equation

HRID 1424145 reaction equation
[C:1]([C:5]1[CH:25]=[CH:24][C:8]2[NH:9][C:10]([C@@:12]([NH:16]C(=O)OC(C)(C)C)([CH3:15])[CH2:13][OH:14])=[N:11][C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[ClH:26]>O1CCOCC1>[NH2:16][C@:12]([C:10]1[NH:9][C:8]2[CH:24]=[CH:25][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][C:7]=2[N:11]=1)([CH3:15])[CH2:13][OH:14].[ClH:26]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178453535HCID 178453535, compound

Product 2

HCID 313Hydrochloric AcidYield 83%HCID 178440687HCID 178440687, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of tert-butyl [(1S)-1-(5-tert-butyl-1H-benzimidazol-2-yl)-2-hydroxy-1-methylethyl]carbamate (Preparation 26, 94 mg, 0.27 mmol) in dioxane (3 mL) was added 4M HCl in dioxane (4 mL) and the reaction stirred at room temperature for 3 hours. The reaction was concentrated in vacuo, azeotroping with toluene (2×10 mL) to afford a gummy solid. The residue was triturated with TBME (15 mL) to afford the title compound as the bis HCl salt (90 mg, 83%).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customazeotroping with toluene (2×10 mL)
  3. customto afford a gummy solid
  4. customThe residue was triturated with TBME (15 mL)

Sources & evidence

ORD record
ord-5fd55a2d50124fe5895e4446704aad2f
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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