Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 1954655Notes

Reaction equation

HRID 1954655 reaction equation
[OH:1]N1C(=O)CCC1=O.CN(C1C=CC=CN=1)C.[CH:18]1([N:24]=[C:25]=[N:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>C(#N)C>[C:25]([NH:24][CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1)([NH:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)=[O:1]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 80170N-Hydroxysuccinimide

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a cooled (0 to 5° C.) solution of DPGS-ω-carboxy-PEG (200 mg), N-hydroxy-succinimide (6 mg), dimethylaminopyridine (DMAP) (2 mg) and acetonitrile (40 mL) in a 250 mL round bottom flask was added dropwise a solution of dicyclohexyl carbodiimide (DCC) (12 mg) in acetonitrile (10 mL). The resulting mixture was stirred for 5 hours and the white solid which formed (dicyclohexylurea) was removed by filtration. The filtrate was concentrated in vacuo to yield 200 mg of a white solid of 3-succinamoyl-oxycarbonyl-polyethyleneglycol-imino-succinate-1,2-dipalmitoyl-sn-glycerol (DPGS-ω-carboxy-PEG-succinimide).

Sources & evidence

ORD record
ord-0e19650975ae47e7be6c4596ec0e97c0
Source dataset
uspto-grants-2000_09
Patent number
US06123923

Reaction notes

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