Dicyclohexylcarbodiimide → HCID 86750348, compound

HRID 1290419Notes

Reaction equation

HRID 1290419 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]([NH:14][CH2:15][C:16]([OH:18])=[O:17])=[O:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].O[N:20]1[C:24](=[O:25])[CH2:23][CH2:22][C:21]1=[O:26].C1(N=C=NC2CCCCC2)CCCCC1>O1CCOCC1.C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][O:11][C:12](=[O:13])[NH:14][CH2:15][C:16]([O:18][N:20]2[C:24](=[O:25])[CH2:23][CH2:22][C:21]2=[O:26])=[O:17])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 10868Dicyclohexylcarbodiimide2×HCID 80170N-HydroxysuccinimideHCID 12187147N-(p-nitrobenzyloxycarbonyl)glycine

Product 1

HCID 86750348HCID 86750348, compoundYield 47.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 2.83 g of product from Example 255 in 43 ml of dioxane is added 1.28 g of N-hydroxysuccinimide and 2.30 g of 1,3-dicyclohexylcarbodiimide, hereinafter called DCC, in 13 ml of dioxane. The formed suspension is stirred at room temperature overnight. The urea by-product is collected and the filtrate is concentrated in vacuo to give an oil. The oil is dissolved in methylene chloride, washed with water, the layers are separated and the organic phase is cooled. The formed crystals are collected and dried to give 1.87 g of the desired product.

Workup

  1. customThe urea by-product is collected
  2. concentrationthe filtrate is concentrated in vacuo
  3. customto give an oil
  4. washwashed with water
  5. customthe layers are separated
  6. temperaturethe organic phase is cooled
  7. customThe formed crystals are collected
  8. customdried

Sources & evidence

ORD record
ord-4494f30bdd70439d984546de6fcd2c00
Source dataset
uspto-grants-1998_05
Patent number
US05750735

Reaction notes

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