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3-[(Triphenylmethyl)sulfanyl]propanoic acid → 11-(p-Tolyloxy)undecyl 3-(tritylthio)propioate

HRID 444611
Notes
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Reaction equation

HRID 444611 reaction equation
[C:1]([S:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(N=C=NCCCN(C)C)C.[C:38]1([CH3:57])[CH:43]=[CH:42][C:41]([O:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55]O)=[CH:40][CH:39]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:1]([S:20][CH2:21][CH2:22][C:23]([O:25][CH2:55][CH2:54][CH2:53][CH2:52][CH2:51][CH2:50][CH2:49][CH2:48][CH2:47][CH2:46][CH2:45][O:44][C:41]1[CH:42]=[CH:43][C:38]([CH3:57])=[CH:39][CH:40]=1)=[O:24])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 2627673-[(Triphenylmethyl)sulfanyl]propanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6754196011-(p-Tolyloxy)undecan-1-ol

Product 1

HCID 6754204611-(p-Tolyloxy)undecyl 3-(tritylthio)propioate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridine
Catalyst
HCID 6344DichloromethaneSolvent

Procedure

The compound 14 (1.86 g), 0.896 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC), and 0.029 g of 4-dimethylaminopyridine (DMAP) were dissolved in 300 ml of methylene chloride. After the compound 16 (3.04 g) was then added and stirred at room temperature for 24 hours, the reaction solution was moved into a separating funnel, and was washed twice with 100 ml of 10% aqueous potassium hydrogen sulfate solution, twice with 100 ml of aqueous saturated sodium hydrogen carbonate solution, twice with 100 ml of ion-exchange water, and twice with 100 ml of saturated brine. After the methylene chloride phase collected was dehydrated with magnesium sulfate, the desiccant agent was removed by filtration, and the solvent of the filtrate was distilled away under reduced pressure. The reaction mixture was purified by chromatography, and 2.63 g of 11-(p-tolyloxy)undecyl 3-(tritylthio)propioate 17, which was a white solid, was obtained.

Workup

  1. customthe reaction solution was moved into a separating funnel
  2. washwas washed twice with 100 ml of 10% aqueous potassium hydrogen sulfate solution, twice with 100 ml of aqueous saturated sodium hydrogen carbonate solution, twice with 100 ml of ion-exchange water
  3. customAfter the methylene chloride phase collected
  4. customthe desiccant agent was removed by filtration
  5. distillationthe solvent of the filtrate was distilled away under reduced pressure
  6. customThe reaction mixture was purified by chromatography, and 2.63 g of 11-(p-tolyloxy)undecyl 3-(tritylthio)propioate 17, which
  7. customwas obtained

Sources & evidence

ORD record
ord-245c61df200e46fc9b62c262e5ea641a
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08475685B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes