tert-Butyldimethylsilyl chloride → HCID 9879821, compound

HRID 642162Notes

Reaction equation

HRID 642162 reaction equation
NCN[C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1.C[CH2:14][N:15](C(C)C)C(C)C.C([Si](C)(C)Cl)(C)(C)C.Cl[C:31]([C:33]1[CH:42]=[CH:41][C:36]([C:37]([O:39][CH3:40])=[O:38])=[CH:35][CH:34]=1)=[O:32]>C1COCC1>[CH3:40][O:39][C:37]([C:36]1[CH:41]=[CH:42][C:33]([C:31]([NH:15][CH2:14][C:4]2[CH:5]=[CH:6][C:7]([C:8]([OH:10])=[O:9])=[CH:11][CH:12]=2)=[O:32])=[CH:34][CH:35]=1)=[O:38]

Participants

6

Reactant 4

HCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 54565033HCID 54565033, compound

Product 1

HCID 9879821HCID 9879821, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a solution of 4-(aminomethyl)amino benzoic acid (5.0 g, 33.1 mmol) in anhydrous THF (200 mL) were added DIEA (12.45 mL, 72.7 mmol) and tert-butyl dimethyl chlorosilane (5.48 g, 36.4 mmol). The resulting mixture was allowed to stir at rt for 1 hr and methyl 4-(chlorocarbonyl)benzoate (7.23 g, 36.4 mmol) was added neat. After overnight stirring at rt, the reaction mixture was quenched with HCl (0.1N, 250 mL) until pH=1. Extraction with EtOAc/THF (400 mL), drying over MgSO4, evaporation under vacuo gave the title compound as a white powder (7.0 g, 67%).

Workup

  1. stirringAfter overnight stirring at rt
  2. customthe reaction mixture was quenched with HCl (0.1N, 250 mL) until pH=1
  3. extractionExtraction with EtOAc/THF (400 mL)
  4. dry with materialdrying over MgSO4, evaporation under vacuo

Sources & evidence

ORD record
ord-6379a30cb9ac4f4f9d90b246bfef69c4
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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