Benzyl Alcohol → 4-Methylbenzene-1-sulfonic acid--benzyl D-leucinate (1/1)

HRID 902220Notes

Reaction equation

HRID 902220 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][C@@H:10]([C:15](O)=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13].O.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25]([OH:28])(=[O:27])=[O:26])=[CH:21][CH:20]=1.O>C1C=CC=CC=1>[S:25]([C:22]1[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=1)([OH:28])(=[O:27])=[O:26].[CH2:1]([O:8][C:15](=[O:16])[C@@H:10]([CH2:11][CH:12]([CH3:14])[CH3:13])[NH2:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 439524D-LeucineHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 446299294-Methylbenzene-1-sulfonic acid--benzyl D-leucinate (1/1)Yield 99%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To benzyl alcohol (8.2 g) dissolved in benzene (30 mL) was added D-leucine (5.0 g) and p-toluenesulfonic acid monohydrate (8.0 g). The reaction was warmed to reflux with removal of water overnight. Once TLC indicated consumption of starting material, the reaction was cooled, and the resulting solid was filtered and washed with EtOAc to give the title compound as a white powder (14.26 g, 99%).

Workup

  1. temperatureThe reaction was warmed
  2. customconsumption of starting material
  3. temperaturethe reaction was cooled
  4. filtrationthe resulting solid was filtered
  5. washwashed with EtOAc

Sources & evidence

ORD record
ord-56413658ab314d7bbf2c7bd669c5d3b6
Source dataset
uspto-grants-2008_04
Patent number
US07365093B2

Reaction notes

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