Benzoyl chloride → HCID 90957134, compound

HRID 2389493Notes

Reaction equation

HRID 2389493 reaction equation
[Cl-].[C:2]([O:6][C:7]([CH2:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[S:19][CH2:20][CH2:21][CH2:22][NH3+:23])=[O:8])([CH3:5])([CH3:4])[CH3:3].CCN(C(C)C)C(C)C.[C:33](Cl)(=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>ClCCl>[C:2]([O:6][C:7](=[O:8])[CH2:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[S:19][CH2:20][CH2:21][CH2:22][NH:23][C:33](=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 69313709HCID 69313709, compound

Product 1

HCID 90957134HCID 90957134, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-(1-tert-butoxycarbonylmethyl-1H-benzoimidazol-2-ylsulfanyl)-propyl-ammonium chloride (Precursor U-08b, 6 mg, 0.02 mmol) in dichloromethane (0.4 ml) are added subsequently DIPEA (10 mg, 15 μl, 0.085 mmol) and benzoyl chloride (3.9 mg, 3.241l, 0.03 mmol) and the resulting solution is allowed to stir for 1 h at rt. Tris-(2-aminoethyl)amine polystyrene (3.4 mmol/g, 33 mg, 0.11 mmol) is added and the mixture is allowed to stir for another 3 h at rt. The solvent is evaporated and the residue dried under high vacuum, yielding the title compound as a colourless oil: tR=2.62 min (LC-2), ESI-MS (pos.): m/z 510.49 [M+H]+.

Workup

  1. stirringto stir for another 3 h at rt
  2. customThe solvent is evaporated
  3. customthe residue dried under high vacuum

Sources & evidence

ORD record
ord-a393331117be4d00830b733908695453
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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