Dichloromethane → N,N'-Dicyclohexylurea

HRID 373297Notes

Reaction equation

HRID 373297 reaction equation
[OH:1]N1C(=O)CCC1=O.[CH:9]1([N:15]=[C:16]=[N:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.C(Cl)Cl>C1COCC1>[C:16]([NH:15][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1)([NH:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)=[O:1]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 10868Dicyclohexylcarbodiimide2×HCID 80170N-Hydroxysuccinimide

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

FMOC-(O-t-Butyl)tyr-val (1.0 gm, 1.8 mMole) and N-hydroxysuccinimide (210 mg, 1.8 mMole) were dissolved in 40 ml THF under nitrogen at 0° C. Dicyclohexylcarbodiimide (DCC) was added as a methylene chloride solution (0.5 M, 3.6 ml, I.8 mMole) and the reaction mixture was incubated for 2 hours with stirring, then stored overnight at 4° C. TLC showed incomplete reaction, so additional DCC was added (0.45 mMole), and the reaction mixture incubated at room temperature for one day. Dicyclohexylurea (DCU) formed was filtered and the filtrate concentrated to a solid, which was triturated with 4% sodium bicarbonate. The solid was filtered, washed with water dried, then crystallized from chloroform/petroleum ether. A white solid was obtained on filtration and air drying. Yield: 761 mg (65%); Rf: 0.75 [chloroform/methanol 9:1 (silica)]. Elemental analysis for C37H41N3O8.0.5 H2O calculated: C, 66.85; H, 6.37; observed C, 67.04; H, 6.85.

Workup

  1. waitstored overnight at 4° C
  2. customreaction
  3. waitthe reaction mixture incubated at room temperature for one day

Sources & evidence

ORD record
ord-1cc5ad39015749159d4e078cafc004b2
Source dataset
uspto-grants-1992_11
Patent number
US05162512

Reaction notes

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