Dicyclohexylcarbodiimide → 1-Decanol

HRID 1420482Notes

Reaction equation

HRID 1420482 reaction equation
[CH2:1](O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11].OCCCCCCCCCC(O)=O.C1(N=C=NC2CCCCC2)CCCCC1.ON1C(=O)CCC1=O>>[CH2:10]([OH:11])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]

Participants

5

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 371531,10-DecanediolHCID 7430010-Hydroxydecanoic AcidHCID 80170N-Hydroxysuccinimide

Product 1

HCID 81741-Decanol

Procedure

Coupling of glycylserylglycylaspartylyaline with 1,10-decanediol. The protected peptide is reacted with 10-hydroxydecanoic acid (Aldrich) in the presence of dicyclohexylcarbodiimide (DCC) (Aldrich) and N-hydroxysuccinimide (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-7d6e1748f53d41378b5587ae06e4130e
Source dataset
uspto-grants-2000_06
Patent number
US06071532

Reaction notes

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