Hydrogen Bromide → N,N'-Dicyclohexylurea

HRID 2293057Notes

Reaction equation

HRID 2293057 reaction equation
Br.N1(C(OCC2C=CC=CC=2)=O)CCC[C@H]1C(O)=[O:5].CN.[CH2:22]1[CH2:27][CH2:26][CH:25]([N:28]=[C:29]=[N:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)[CH2:24][CH2:23]1>C(Cl)Cl>[C:29]([NH:28][CH:25]1[CH2:24][CH2:23][CH2:22][CH2:27][CH2:26]1)([NH:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)=[O:5]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 6329MethylamineHCID 10868DicyclohexylcarbodiimideHCID 101987Benzyloxycarbonyl-L-proline

Product 1

HCID 4277N,N'-DicyclohexylureaYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution of the phosphonate 4-CN-PheP (OPh)2.HBr (0.41 g, 0.9 mmole) and Cbz-Pro-OH (0.25 g, 1.0 mmole) in 20 mL CH2Cl2 was added 0.14 mL Methyl amine. After stirring for 10 min, DCC (0.21 g, 1.0 mmole) was added and the mixture was stirred at 0° C. for 2 h and at r.t. for 24 h. During this period, dicyclohexylurea (DCU) formed, was removed by filtration and the filtrate was evaporated. The residue was dissolved in 50 mL ethyl acetate, filtered, the filtrate was washed with 50 mL 1N HCl, water, 6% NaHCO3, and water. The organic layer was dried, filtered, and evaporated to give crude product which was then recrystallized from ether to give white crystals, yield 52% (0.29 g); mp 131°-132° C.; 1H NMR (DMSO) δ8.75(m, 1H), 7.8-7.2(m, 19H), 5.06 (m, 2H), 4.95 (m, 1H), 4.6 (q, 1H), 4.2 (m, 1H), 3.5-3.1 (m, 3H), 2.0-1.4 (m, 4H); MS (FAB+) m/e 610 (M+1). Anal. (C34H32N3O6P) C, H, N.

Workup

  1. stirringthe mixture was stirred at 0° C. for 2 h and at r.t. for 24 h
  2. waitDuring this period

Sources & evidence

ORD record
ord-006abf54aad646ca976d5b772c657b0b
Source dataset
uspto-grants-1997_11
Patent number
US05686419

Reaction notes

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