Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 1647559Notes

Reaction equation

HRID 1647559 reaction equation
CC([C@]1(O)[C@@]2(C)[C@]3(O)[C@]45O[C@@]2(O)C[C@@](C)([C@@]4(O)CCC([C@H]5[OH:19])=C)[C@]3(O)[C@@H]1OC(C1NC=CC=1)=O)C.C(OC1C=CC(C(NCCC(O)=O)=O)=CC=1)CCC.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH:69]1([N:75]=[C:76]=[N:77][CH:78]2[CH2:83][CH2:82][CH2:81][CH2:80][CH2:79]2)[CH2:74][CH2:73][CH2:72][CH2:71][CH2:70]1>CN(C1C=CN=CC=1)C.C(Cl)Cl.O1CCCC1.O>[C:76]([NH:75][CH:69]1[CH2:70][CH2:71][CH2:72][CH2:73][CH2:74]1)([NH:77][CH:78]1[CH2:83][CH2:82][CH2:81][CH2:80][CH2:79]1)=[O:19]

Participants

9

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 14812Phosphorus oxide (P4O10)HCID 1251684,6,7,8a,8b,9a-Hexahydroxy-6a,9-dimethyl-3-methylidene-7-(propan-2-yl)dodecahydro-6,9-methanobenzo[1,2]pentaleno[1,6-bc]furan-8-yl 1H-pyrrole-2-carboxylateHCID 22183723-[(4-butoxybenzoyl)amino]propanoic Acid

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dehydro-ryanodine (60 mg., 0.125 mmol), N-(p-n-butoxybenzoyl)-β-alanine (40 mg. 0.15 mmol) and DMAP (2 mg., 0.02 mmol), dried over P2O5, were dissolved in a solvent mixture of CH2Cl2 (10 ml.) and tetrahydrofuran (0.1 ml) dried over Molecular Sieve. To the stirred solution dicyclohexylcarbodiimide (35 mg., 0.15 mmol) was added at once and the reaction mixture maintained at room temperature for 6 hours. Water (0.1 ml) was added and stirring continued for 30 minutes. The solids formed (dicyclohexylurea) were filtered and washed twice with CH2Cl2.

Workup

  1. customdried over Molecular Sieve

Sources & evidence

ORD record
ord-60e7bdc3862746d98c129efceea07f03
Source dataset
uspto-grants-1995_07
Patent number
US05432288

Reaction notes

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