Sodium Hydroxide → HCID 11818169, compound

HRID 2301272Notes

Reaction equation

HRID 2301272 reaction equation
[NH2:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].[OH-].[Na+].[CH2:17]([O:20][C:21](Cl)=[O:22])[CH:18]=[CH2:19]>O.O1CCOCC1>[CH2:17]([O:20][C:21]([NH:1][C@@H:2]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]#[N:14])=[CH:11][CH:12]=1)[C:3]([OH:5])=[O:4])=[O:22])[CH:18]=[CH2:19]

Participants

6

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 18052Allyl chloroformateHCID 1501865(L)-4-Cyanophenylalanine

Product 1

HCID 11818169HCID 11818169, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A suspension of 50 g (0.221 mol) of (S)-2-amino-3-(4-cyanophenyl)propionic acid in 150 ml of water was adjusted to pH=8 with 1N NaOH. 26.6 g (0.221 mol) of allylchloroformate in 225 ml of dioxane were slowly added at 0 to 5° C. (pH kept at 8 by addition of 1N NaOH). After completion of the reaction (thin layer chromatography (TLC) control) the mixture was extracted with DCM and the aqueous layer was acidified to pH=2 with KHSO4. The precipitate was dissolved in DCM, dried (Na2SO4), and evaporated. The residue was recrystallized from ether/petroleum benzene to give 31 g (51%) of the title compound. MS=275.1 (M+1)+.

Workup

  1. customAfter completion of the reaction (thin layer chromatography (TLC) control) the mixture
  2. extractionwas extracted with DCM
  3. dissolutionThe precipitate was dissolved in DCM
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was recrystallized from ether/petroleum benzene

Sources & evidence

ORD record
ord-6555096d1b8f4fa7b508efbea1774a40
Source dataset
uspto-grants-2002_12
Patent number
US06500803B1

Reaction notes

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