Dicyclohexylcarbodiimide → 1-Decanol

HRID 565167Notes

Reaction equation

HRID 565167 reaction equation
NCC(N[C@H](C(NCC(N[C@H](C(N[C@H](C(O)=O)C(C)C)=O)CC(=O)O)=O)=O)CO)=O.[CH2:31](O)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][OH:41].OCCCCCCCCCC(O)=O.C1(N=C=NC2CCCCC2)CCCCC1.ON1C(=O)CCC1=O>>[CH2:40]([OH:41])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH3:31]

Participants

6

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 371531,10-DecanediolHCID 7430010-Hydroxydecanoic AcidHCID 80170N-HydroxysuccinimideHCID 54459949Glycylserylglycylaspartylvaline

Product 1

HCID 81741-Decanol

Procedure

Coupling of glycylserylglycylaspartylvaline with 1,10-decanediol. The protected peptide is reacted with 10-hydroxydecanoic acid (Aldrich) in the presence of dicyclohexylcarbodiimide (DCC) (Aldrich) and N-hydroxy-succinimide (Aldrich) according to Bergeron et al. (1981) J. Org. Chem. 46:4524, until the complete consumption of the peptide starting material is confirmed by thin layer chromatography. Flash column purification gives 10-(peptidyloxy) decanol as product, through formation of an amide linkage.

Workup

  1. custom46:4524, until the complete consumption of the peptide starting material
  2. customFlash column purification

Sources & evidence

ORD record
ord-90ae0101f6e74a0383a29df67f6e8c24
Source dataset
uspto-grants-2001_01
Patent number
US06171614B2

Reaction notes

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