Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 1721467Notes

Reaction equation

HRID 1721467 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.IC1C=CC(C(NCCC(O)=O)=O)=CC=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH:65]1([N:71]=[C:72]=[N:73][CH:74]2[CH2:79][CH2:78][CH2:77][CH2:76][CH2:75]2)[CH2:70][CH2:69][CH2:68][CH2:67][CH2:66]1>CN(C1C=CN=CC=1)C.C(Cl)Cl.O1CCCC1.O>[C:72]([NH:71][CH:65]1[CH2:66][CH2:67][CH2:68][CH2:69][CH2:70]1)([NH:73][CH:74]1[CH2:79][CH2:78][CH2:77][CH2:76][CH2:75]1)=[O:19]

Participants

9

Reactant 4

HCID 10868Dicyclohexylcarbodiimide2×HCID 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 22902432HCID 22902432, compound

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 4

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

Procedure

Dehydroryanodine (100 mg, 0.2 mmol), N-(p-iodobenzoyl)-β-alanine (50 mg, 0.22 mmol) and DMAP (2 mg, 0.02 mmol), all 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 (DCC, 52 mg., 0.25 mmol) was added at once and the stirred reaction maintained at room temperature for 6 hours. Water (0.1 ml) was added to inactivate excess DCC and stirring was continued for 30 minutes. The crystals of dicyclohexylurea thus formed were filtered off and washed twice with CH2Cl2.

Workup

  1. customdried over Molecular Sieve
  2. customthe stirred reaction

Sources & evidence

ORD record
ord-3ae35235d3aa422faa1cab132c0edf38
Source dataset
uspto-grants-1996_04
Patent number
US05510500

Reaction notes

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