Dicyclohexylcarbodiimide → Fmoc-Phe-OSu

HRID 1767035Notes

Reaction equation

HRID 1767035 reaction equation
[NH:1]([C:13]([O:15][CH2:16][CH:17]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]2[C:18]1=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:14])[C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O[N:31]1[C:35](=[O:36])[CH2:34][CH2:33][C:32]1=[O:37].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[NH:1]([C:13]([O:15][CH2:16][CH:17]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]2[C:18]1=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:14])[C@H:2]([C:10]([O:12][N:31]1[C:35](=[O:36])[CH2:34][CH2:33][C:32]1=[O:37])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 978331Fmoc-phenylalanine

Product 1

HCID 11826988Fmoc-Phe-OSuYield 113.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of Fmoc-Phe (1.9442 g, 5.0186 mmol, 1.0 eq) and N-hydroxysuccinimide (0.6095 g, 5.2959 mmol, 1.06 eq) in methylene chloride (50 ml) cooled in an ice bath, was added DCC (1.0880 g, 5.2731 mmol, 1.05 eq). The mixture was stirred at room temperature overnight. The resulting DCU was removed by filtration and the filtrate was condensed and dried in vacuo to give 2.7664 g of white foam.

Workup

  1. temperaturecooled in an ice bath
  2. customThe resulting DCU was removed by filtration
  3. customcondensed
  4. customdried in vacuo

Sources & evidence

ORD record
ord-15748c3837e74e9596510129f35253e7
Source dataset
uspto-grants-2007_06
Patent number
US07232805B2

Reaction notes

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