Dicyclohexylcarbodiimide → HCID 67710918, compound

HRID 1720297Notes

Reaction equation

HRID 1720297 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([O:23][C:24]([N:26]1[CH2:33][CH:32]([O:34][CH2:35][O:36][CH3:37])[CH2:31][C@H:27]1[C:28]([OH:30])=O)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH:38]1([CH2:44][NH2:45])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1.ON1C(=O)CCC1=O>O1CCOCC1>[CH2:16]([O:23][C:24]([N:26]1[CH2:33][CH:32]([O:34][CH2:35][O:36][CH3:37])[CH2:31][C@H:27]1[C:28]([NH:45][CH2:44][CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1)=[O:30])=[O:25])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 76688CyclohexanemethylamineHCID 80170N-HydroxysuccinimideHCID 54042102HCID 54042102, compound

Product 1

HCID 67710918HCID 67710918, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

13.4 g of dicyclohexylcarbodiimide was added, at room temperature, to a solution of 19.3 g of 1-benzyloxycarbonyl-4-methoxymethoxy-L-proline, 8.5 ml of cyclohexylmethylamine and 7.5 g of N-hydroxysuccinimide in 200 ml of dioxane. The mixture was stirred at the same temperature for 2 hours, then heated at 60° C. for 1 hour, and allowed to cool, followed by filtration. The solvent in the filtrate was removed by filtration. The resulting residue was purified by a silica gel column chromatography (eluant; 5% methanol/chloroform) to obtain 21.2 g of N-(1-benzyloxycarbonyl-4-methoxymethoxy-L-prolyl)-N-cyclohexylmethylamine as a light yellow oil.

Workup

  1. temperatureto cool
  2. filtrationfollowed by filtration
  3. customThe solvent in the filtrate was removed by filtration
  4. customThe resulting residue was purified by a silica gel column chromatography (eluant; 5% methanol/chloroform)

Sources & evidence

ORD record
ord-e1801c9333174f149fc3b00fb79c8d79
Source dataset
uspto-grants-1996_04
Patent number
US05506239

Reaction notes

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