N,N'-Dicyclohexylurea → N-Oleoyl-L-Serine

HRID 218120Notes

Reaction equation

HRID 218120 reaction equation
[C:1]([OH:20])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].ON1[C:26](=[O:27])CCC1=O.C1([N:35]=C=NC2CCCCC2)CCCCC1.C(NC1CCCCC1)(NC1CCCCC1)=O.[C:60]([O:63]CC)(=[O:62])[CH3:61]>>[C:1]([NH:35][C@H:61]([C:60]([OH:63])=[O:62])[CH2:26][OH:27])(=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 5

HCID 4277N,N'-DicyclohexylureaHCID 8857Ethyl Acetate2×HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 445639Oleic Acid2×

Product 1

HCID 44190514N-Oleoyl-L-Serine

Procedure

N-Hydroxysuccinimide Ester of Oleic Acid. Oleic acid (2 g, 7.08 mmoles) was added to a solution of N-hydroxysuccinimide (0.814 g, 7.08 mmoles) in dry ethyl acetate (30 ml). A solution of dicyclohexylcarbodiimide (1.45 g, 7.08 mmoles) in dry ethyl acetate (2.5 ml) was then added, and the reaction mixture was left overnight at room temperature Dicyclohexylurea was filtered, and the crude material was chromatographed on silica gel (eluting with chloroform) to give 2.38 g (85%) as yellowish oil.

Workup

  1. filtrationwas filtered
  2. customthe crude material was chromatographed on silica gel (eluting with chloroform)
  3. customto give 2.38 g (85%) as yellowish oil

Sources & evidence

ORD record
ord-219a14d9b8744b5e8d4a0ec80c03c63e
Source dataset
uspto-grants-2012_06
Patent number
US08198327B2

Reaction notes

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