Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 1968412Notes

Reaction equation

HRID 1968412 reaction equation
C[O:2]C(=O)CCCCC(O)=O.[CH2:12]1[CH2:17][CH2:16][CH:15]([N:18]=[C:19]=[N:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[CH2:14][CH2:13]1.ON1C(=O)CCC1=O>CN(C1C=CN=CC=1)C.CN(C=O)C>[C:19]([NH:18][CH:15]1[CH2:14][CH2:13][CH2:12][CH2:17][CH2:16]1)([NH:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:2]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 12328monoMethyl adipateHCID 80170N-Hydroxysuccinimide

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Step 1, Compound 4: Adipic acid monomethyl ester is treated with one molar equivalent of DCC, DMAP and N-hydroxysuccinimide in DMF for 30 min. To this a molar equivalent of the compound obtained from Step 3a (Example 1) is added and stirred at ambient temperature for 8 h. Dicylcohexylurea formed during the course of the reaction is filtered off and the product is extracted into ethyl acetate, washed with sodium bicarbonate solution followed by standard workup. The methyl ester thus obtained is treated with LiOH in THF/water to obtain compound 4.

Sources & evidence

ORD record
ord-7ef89d4de04d4bb8acc9d7a8fbe7b213
Source dataset
uspto-grants-2013_04
Patent number
US08426377B2

Reaction notes

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