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Stearic Acid → N-Succinimidyl Stearate

HRID 1970779
Notes
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Reaction equation

HRID 1970779 reaction equation
[C:1]([OH:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].O[N:22]1[C:26](=[O:27])[CH2:25][CH2:24][C:23]1=[O:28].Cl.C(N=C=NCCCN(C)C)C.S([O-])([O-])(=O)=O.[Mg+2]>ClCCl.O>[CH3:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([O:20][N:22]1[C:26](=[O:27])[CH2:25][CH2:24][C:23]1=[O:28])=[O:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 5281Stearic AcidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 3552761N-Succinimidyl Stearate

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6344DichloromethaneSolvent

Procedure

1.87 g of stearic acid was dissolved in 50 ml of dichloromethane, to which 0.76 g of N-hydroxysuccinimide and 1.25 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride were added and stirred at room temperature for 24 hours. After the reaction, the solution was combined with 100 ml of water and subjected to liquid-liquid separation using a separatory funnel. The organic phase obtained was dehydrated with magnesium sulfate, and enriched using an evaporator. The enriched solution was added dropwise to 20 volumes of ethanol to form a white precipitate, which was collected by filtration and dried under reduced pressure to obtain N-succinimidyl stearate.

Workup

  1. additionwere added
  2. customAfter the reaction
  3. customsubjected to liquid-liquid separation
  4. customThe organic phase obtained
  5. customan evaporator
  6. additionThe enriched solution was added dropwise to 20 volumes of ethanol
  7. customto form a white precipitate, which
  8. filtrationwas collected by filtration
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-f86148798cf648f0bb60c18cda6c32ed
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08431545B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes