Acetic Acid → di-tert-butyl 2,2'-((2-(2-(((4-sulfamoylphenethyl)(thiazol-2-ylmethyl)amino)methyl)-1H-imidazol-1-yl)acetyl)azanediyl)diacetate

HRID 1484605Notes

Reaction equation

HRID 1484605 reaction equation
[S:1]([C:5]1[CH:39]=[CH:38][C:8]([CH2:9][CH2:10][NH:11][CH2:12][C:13]2[N:14]([CH2:18][C:19]([N:21]([CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:20])[CH:15]=[CH:16][N:17]=2)=[CH:7][CH:6]=1)(=[O:4])(=[O:3])[NH2:2].[S:40]1[CH:44]=[CH:43][N:42]=[C:41]1[CH:45]=O.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.O>[S:1]([C:5]1[CH:39]=[CH:38][C:8]([CH2:9][CH2:10][N:11]([CH2:12][C:13]2[N:14]([CH2:18][C:19]([N:21]([CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:22][C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])=[O:20])[CH:15]=[CH:16][N:17]=2)[CH2:45][C:41]2[S:40][CH:44]=[CH:43][N:42]=2)=[CH:7][CH:6]=1)(=[O:3])(=[O:4])[NH2:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 27349031,3-Thiazole-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 71521810di-tert-butyl 2,2'-((2-(2-(((4-sulfamoylphenethyl)amino)methyl)-1H-imidazol-1-yl)acetyl)azanediyl)diacetate

Product 1

HCID 86692721di-tert-butyl 2,2'-((2-(2-(((4-sulfamoylphenethyl)(thiazol-2-ylmethyl)amino)methyl)-1H-imidazol-1-yl)acetyl)azanediyl)diacetateYield 70.2%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

To a solution of di-tert-butyl 2,2′-((2-(2-(((4-sulfamoylphenethyl)amino)methyl)-1H-imidazol-1-yl)acetyl)azanediyl)diacetate (244 mg, 0.43 mmol), thiazole-2-carbaldehyde (68 mg, 0.61 mmol), AcOH (0.05 mL) in DCE (10 mL) at 0° C. was treated with NaBH(OAc)3 (212 mg, 1.0 mmol). The reaction mixture was stirred at room temperature for 2 hrs and decomposed with water. The reaction mixture was concentrated under reduced pressure to give a residue. The residue was purified by biotage over silica gel to afford di-tert-butyl 2,2′-((2-(2-(((4-sulfamoylphenethyl)(thiazol-2-ylmethyl)amino)methyl)-1H-imidazol-1-yl)acetyl)azanediyl)diacetate as a colorless oil (200 mg, 70%). MS (ESI), 663.3 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto give a residue
  3. customThe residue was purified by biotage over silica gel

Sources & evidence

ORD record
ord-108b57a0d54d4d55a7ed5067cc61b4ec
Source dataset
uspto-grants-2016_08
Patent number
US09422251B2

Reaction notes

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