1,4-Dioxane → HCID 86750199, compound

HRID 862014Notes

Reaction equation

HRID 862014 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-8c0c22de3f234c29945ddafdb61c6d00
Source dataset
uspto-grants-1998_02
Patent number
US05716979

Reaction notes

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