Dicyclohexylcarbodiimide → N-(N'-acetylsarcosyl)-N-benzylglycine ethylester

HRID 745202Notes

Reaction equation

C1CCC(N=C=NC2CCCCC2)CC1.[C:16]([N:19]([CH2:21][C:22](O)=[O:23])[CH3:20])(=[O:18])[CH3:17].[CH2:25]([O:27][C:28](=[O:38])[CH2:29][NH:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH3:26]>CN(C)C=O.C(Cl)(Cl)Cl>[CH2:25]([O:27][C:28](=[O:38])[CH2:29][N:30]([C:22](=[O:23])[CH2:21][N:19]([C:16](=[O:18])[CH3:17])[CH3:20])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH3:26]

Participants

Conditions

Temperature: 0 °C

Procedure

A cold solution of 1.65 g DCC in 3 ml dimethylformamide is added to a stirred ice-cooled solution of 1.0 g N-acetylsarcosine and 1.4 g N-benzylglycine ethylester in 9 ml dry dimethylformamide, and the resulting solution is stirred at 0° C. for 1 hour and then at room temperature for 2 hours. It is then filtered and the precipitate is washed with dimethylformamide. The filtrate and washings are combined and the solvent is evaporated to dryness in vacuo to yield a residue which is then dissolved in 30 ml chloroform, washed with 5% aq. NaHCO3 and water, and dried over anhydrous MgSO4. Evaporation of solvent produces the desired ester which is either isolated (m.p. 98°-101° C.) or hydrolyzed directly to form the corresponding acid, N-(N'-acetylsarcosyl)-N-benzylglycine.

Workup

waitat room temperature for 2 hours
filtrationIt is then filtered
washthe precipitate is washed with dimethylformamide
customthe solvent is evaporated to dryness in vacuo
customto yield a residue which
washwashed with 5% aq. NaHCO3 and water
dry with materialdried over anhydrous MgSO4
customEvaporation of solvent

Sources & evidence

ORD record: ord-a3f498193a4742e5beb57533f865eb26
Source dataset: uspto-grants-1986_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04598067

Reaction notes

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