Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 271037Notes

Reaction equation

HRID 271037 reaction equation
CCCCCCCCCCCCCCCC(OC[C@@H](OC(CCCCCCCCCCCCCCC)=O)COC(CCC(O)=O)=O)=[O:17].ON1C(=O)CCC1=O.[CH2:56]1[CH2:61][CH2:60][CH:59]([N:62]=[C:63]=[N:64][CH:65]2[CH2:70][CH2:69][CH2:68][CH2:67][CH2:66]2)[CH2:58][CH2:57]1>CN(C1C=CN=CC=1)C.C(#N)C>[C:63]([NH:62][CH:59]1[CH2:58][CH2:57][CH2:56][CH2:61][CH2:60]1)([NH:64][CH:65]1[CH2:70][CH2:69][CH2:68][CH2:67][CH2:66]1)=[O:17]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 1300201,2-Dipalmitoyl-3-succinylglycerol

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent2×

Procedure

To a cooled (0 to 5° C.) solution of 1,2-dipalmitoyl-sn-glycero-3-succinate (66.8 mg), N-hydroxy-succinimide (11.5 mg), DMAP (2 mg) and acetonitrile (40 mL) in a 100 mL round bottom flask was added dropwise a solution of DCC (20.6 mg) in acetonitrile (10 mL). The resulting mixture was stirred for 5 hours. The solid material which formed during the reaction (dicyclohexylurea) was removed by filtration and the filtrate was concentrated in vacuo to yield 78 mg of N-DPGS-succinimide as a white product.

Sources & evidence

ORD record
ord-5958eb1554b740b6982cf319b6af5d9a
Source dataset
uspto-grants-2008_11
Patent number
US07452551B1

Reaction notes

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