Hydrochloric Acid → HCID 69318555, compound

HRID 2389498Notes

Reaction equation

HRID 2389498 reaction equation
[C:1]([O:5][C:6](=[O:28])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[S:17][CH2:18][CH2:19][NH:20]C(OC(C)(C)C)=O)([CH3:4])([CH3:3])[CH3:2].[ClH:29]>CCOC(C)=O>[Cl-:29].[C:1]([O:5][C:6]([CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[S:17][CH2:18][CH2:19][NH3+:20])=[O:28])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 91275966HCID 91275966, compound

Product 1

HCID 69318555HCID 69318555, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tert-butyl[2-(2-tert-butoxycarbonylamino-ethylsulfanyl)-benzoimidazol-1-yl]-acetate (Precursor V-02b) is dissolved in 3M HCl in AcOEt and stirred for 1 h at rt. Evaporation of the solvent in vacuo yields 2-(1-tert-butoxycarbonylmethyl-1H-benzoimidazol-2-ylsulfanyl)-ethyl-ammonium chloride as a colourless solid. To a solution of n-butylchloroformate (14.9 mg, 14 μl, 0.11 mmol) in dry THF (0.5 ml) cooled to 0° C. is added a solution of HOBt (17.3 mg, 0.11 mmol) and DIPEA (18 mg, 23.8 μl, 0.14 mmol) in dry THF (0.5 ml). The resulting mixture is stirred for 10 min. It is then added dropwise at 0° C. onto a solution of 2-(1-tert-butoxycarbonylmethyl-1H-benzoimidazol-2-ylsulfanyl)-ethyl-ammonium chloride (30 mg, 0.09 mmol) and DIPEA (11.2 mg, 14.9 μl, 0.09 mmol) in dry THF (0.7 ml). The resulting mixture is stirred for 1 h at rt. Then tris-(2-aminoethyl)amine polystyrene (3.4 mmol/g, 25.6 mg) is added and the resulting slurry is allowed to stir for 2 h at rt and then filtered. The solvent is removed in vacuo and the residue is diluted with dichloromethane (5 ml). This organic phase is washed once with a saturated aqueous NaHCO3 solution and a saturated aqueous KH2PO4 solution. Evaporation of the solvent in vacuo yields the title compound (17.1 mg) in 48% as a colourless oil: tR=2.35 min (LC-2), ESI-MS (pos.): m/z 408.29 [M+H]+.

Workup

  1. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-0ede81a6bbae44d7ae91c2e2187cf016
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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