Pyridine → Oleoyl Serinate

HRID 707632Notes

Reaction equation

HRID 707632 reaction equation
C([NH:8][C@H:9]([C:12]([OH:14])=[O:13])[CH2:10][OH:11])(OC(C)(C)C)=O.[C:15](Cl)(=[O:33])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].C(N[C@H](C(O)=O)CO)(=O)CCCCCCC/C=C\CCCCCCCC.N1C=CC=CC=1>C(Cl)(Cl)Cl>[NH2:8][C@H:9]([C:12]([O:14][C:15](=[O:33])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:13])[CH2:10][OH:11]

Participants

6

Reactant 4

HCID 1049PyridineHCID 98766N-[tert-butoxycarbonyl]-L-serineHCID 5364783Oleoyl chloride2×HCID 44190514N-Oleoyl-L-Serine

Product 1

HCID 86669080Oleoyl Serinate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

0.03 moles of N-Boc-serine was constantly stirred under nitrogen in 100 mL of chloroform. 0.03 mole of oleoyl chloride was dissolved with 100 mL of chloroform and added to this heterogeneous mixture of N-Oleoylserine and followed by adding 10 mL of anhydrous pyridine. The reaction for 30 minutes under constantly stirring at room temperature, the mixture turned to homogeneous and the reaction was completed when no detectable oleoyl chloride was in the mixture. The bulk solvent was removed under vacuum and the crude product was used to next step without further purification. The resulting product (% of yields 75-80) is showed in Chemical Structure 4.

Workup

  1. customThe reaction for 30 minutes
  2. customThe bulk solvent was removed under vacuum
  3. customthe crude product was used to next step without further purification
  4. customThe resulting product (% of yields 75-80)

Sources & evidence

ORD record
ord-87d9fddef19543e4a731086e5c1d76b5
Source dataset
uspto-grants-2015_11
Patent number
US09175027B2

Reaction notes

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