Benzyl Alcohol → Boc-Iminodiacetic acid dibenzyl ester

HRID 1740724Notes

Reaction equation

[C:1]([CH:8]([NH:12][CH2:13][C:14]([OH:16])=[O:15])[C:9]([OH:11])=[O:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:17](O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH:25]1[CH:26]=[CH:27][C:28]2N(O)N=N[C:29]=2[CH:30]=1.[CH2:35]1CCC(N=C=NC2CCCCC2)CC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:17]([O:15][C:14](=[O:16])[CH2:13][NH:12][CH:8]([C:1]([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2])[C:9]([O:11][CH2:35][C:29]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:30]=1)=[O:10])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Boc-Iminodiacetic acid (5 g, 21.44 mmol), 4-dimethylaminopyridine (5.24 g, 42.87 mol), benzyl alcohol (4.64 g, 42.9 mmol) and HOBt (6.8 g, 43 mmol) were dissolved in CH2Cl2 (200 mL) and the solution was cooled to 0° C. DCC (8.84 g, 42.9 mmol) was added and the reaction was allowed to proceed at ambient temperature overnight. Precipitated dicyclohexylurea was filtered off and the filtrated was extracted with 4% aq NaHCO3.

Workup

filtrationPrecipitated dicyclohexylurea was filtered off
extractionthe filtrated was extracted with 4% aq NaHCO3

Sources & evidence

ORD record: ord-ee1b608f8a754311ace9c7fd072f6371
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05972926

Reaction notes

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