Dichloromethane → (3-Benzyloxybenzyl) iminodicarboxylic acid di-tert-butyl ester

HRID 2080036Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32]Cl)[CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.ClCCl>CN(C)C=O.O>[C:12]([O:11][C:9]([N:8]([CH2:32][C:28]1[CH:29]=[CH:30][CH:31]=[C:26]([O:25][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:27]=1)[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[O:10])([CH3:15])([CH3:14])[CH3:13]

Participants

Conditions

Temperature: 60 °C

Procedure

Next, to a solution of iminodicarboxylic acid di-tert-butyl ester (2.12 g, 8.76 mmol) in N,N-dimethylformamide (13 mL) was added sodium hydride (0.39 g, 9.86 mmol, 60% in oil), the solution was stirred at 60° C. for 6 hours, 1-benzyloxy-3-chloromethyl-benzene (1.0 g, 4.30 mmol) was added, and the solution was further stirred at 60° C. for 4 hours. The reaction solution was allowed to room temperature, then, dichloromethane and water were added for partitioning, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated, then, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1), and (3-benzyloxybenzyl)iminodicarboxylic acid di-tert-butyl ester (691 mg, 39%) was obtained as a pale yellow oil.

Workup

stirringthe solution was further stirred at 60° C. for 4 hours
customwas allowed to room temperature
customfor partitioning
dry with materialthe organic layer was dried over anhydrous magnesium sulfate
customThe solvent was evaporated
customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record: ord-cb1b86b4e84c44fa8c37a87665ff7c2e
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932272B2

Reaction notes

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