Dicyclohexylcarbodiimide → HCID 69648787, compound

HRID 2300023Notes

Reaction equation

HRID 2300023 reaction equation
[C:1]([NH:11][CH2:12][CH2:13][C:14]([OH:16])=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].ON1[C:22](=[O:23])[CH2:21]CC1=O.C1CCC([N:31]=C=NC2CCCCC2)CC1>C1COCC1>[C:1]([NH:11][CH2:12][CH2:13][C:14]([CH:22]([CH2:21][NH2:31])[OH:23])=[O:16])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 75313N-Benzyloxycarbonyl-beta-alanineHCID 80170N-Hydroxysuccinimide

Product 1

HCID 69648787HCID 69648787, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a THF solution of N-(CBZ)-β-alanine and N-hydroxysuccinimide, add DCC. The reaction is mixed overnight at room temperature. The crude reaction mixture is filtered through a sintered glass funnel into a round bottom flask to remove the DCU that is formed. The activated ester should remain in solution. After concentrating and redissolving in solvent, ethanolamine or an alcohol protected derivative can be added as a solution to the solution containing the activated ester. Triethylamine can also be added. Workup of the reaction and purification results in formation of N-carbobenzoxy-β-alanyl-ethanolamine. The free alcohol can be sulfated by a variety of methods to result in formation of N-carbobenzoxy-β-alanyl-ethanolamine sulfate.

Workup

  1. additionThe reaction is mixed overnight at room temperature
  2. customThe crude reaction mixture
  3. filtrationis filtered through a sintered glass funnel into a round bottom flask
  4. customto remove the DCU that
  5. customis formed
  6. concentrationAfter concentrating
  7. dissolutionredissolving in solvent, ethanolamine
  8. additionan alcohol protected derivative can be added as a solution to the solution
  9. additioncontaining the activated ester
  10. additionTriethylamine can also be added
  11. customWorkup of the reaction and purification

Sources & evidence

ORD record
ord-a67825ceba4d4468afdd00523eccf3a7
Source dataset
uspto-grants-2002_12
Patent number
US06498150B2

Reaction notes

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