1,4-Dioxane → HCID 86750199, compound

HRID 341871Notes

Reaction equation

HRID 341871 reaction equation
C[N:2]([C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[C@:3]([CH3:17])([C:14]([OH:16])=[O:15])[CH2:4][C:5]1[S:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[CH:9]=1.O.[OH-].[Li+].O1CCOCC1>O>[C:18]([NH:2][C@:3]([CH3:17])([C:14]([OH:16])=[O:15])[CH2:4][C:5]1[S:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[CH:9]=1)([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 168937Lithium hydroxide, monohydrateHCID 86750197HCID 86750197, compound

Product 1

HCID 86750199HCID 86750199, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of methyl N-CBZ-α-methyl-3-benzothiophenylalanine (0.6 g, 1.57 mmol), lithium hydroxide hydrate (0.14 g, 3.33 mmol) in water (20 mL), and dioxan (20 mL) was stirred at room temperature overnight. The reaction mixture was diluted with water, washed with ether, acidified with 1N hydrochloric acid, and extracted with ethyl acetate three times. The combined extracts were washed with water, dried over magnesium sulphate, filtered, and evaporated to dryness. Crystallization from ether/hexane gave colorless crystals 0.48 g (83%); mp 133°-135° C.;

Workup

  1. washwashed with ether
  2. extractionextracted with ethyl acetate three times
  3. washThe combined extracts were washed with water
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customCrystallization from ether/hexane

Sources & evidence

ORD record
ord-af574a8b4c9d4aba80e3da1d08e9e9dc
Source dataset
uspto-grants-1999_01
Patent number
US05856354

Reaction notes

Loading…