Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 2395226Notes

Reaction equation

HRID 2395226 reaction equation
[OH:1]N1C(=O)CCC1=O.[CH:9]1([N:15]=[C:16]=[N:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>CN(C)C=O>[CH:18]1([NH:17][C:16]([NH:15][CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)=[O:1])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 80170N-Hydroxysuccinimide

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

(1-Carboxymethyl-3-hydroxy-2-methyl-pyrid-4-one)3 -AL+3 (4.5 g) in 200 ml of dimethylformamide (DMF) has added N-hydroxysuccinimide (2.9 g! followed by addition of dicyclohexylcarbodiimide (5.2 g) dissolved in 100 ml of DMF, is stirred and left to stand over night. The reaction produces a white precipitate, N,N'-dicyclohexylurea that is filtered off and discarded. Glucosamine [5.4 g] is added to the filtrate and allowed to react for 2 h, and then the pH is adjusted to 2.5 with sulphuric acid and rotary evaporated to dryness and is then extracted with several volumes of hot methanol. The combined extracts are concentrated until precipitation begins after which the solution is stored in refrigerator over night to complete precipitation of 2-deoxy-2-(N-carbamoylmethyl-[N'-2'-methyl-3'-hydroxypyrid-4'-one])-D-glucopyranose. Molecular mass, M+=382.8, by mass spectroscopy. The compound dissolved in ethanol/water mixture with added iron forms the purple coloured complex. HPLC analysis of mixture of 3-hydroxy-2-methyl-4-pyrone control and synthetic end product which showed a single sharp peaks well separated from the control.

Workup

  1. waitleft
  2. waitto stand over night

Sources & evidence

ORD record
ord-dfb47c7195af40bd820a01ecd62b17e9
Source dataset
uspto-grants-1998_09
Patent number
US05814614

Reaction notes

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