Benzyl chloroformate → HCID 22994173, compound

HRID 397675Notes

Reaction equation

HRID 397675 reaction equation
[OH-].[Na+].[NH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1.Cl[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]>O1CCOCC1.O>[CH2:21]([O:20][C:18]([NH:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1)=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformate2×HCID 14798Sodium HydroxideHCID 18763694HCID 18763694, compound

Product 1

HCID 22994173HCID 22994173, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

Sodium hydroxide (222 mg) was added to a solution of 2-[4-(2-aminoethoxy)-phenyl]acetic acid (394 mg) (see DE-A-2250400) in 1,4-dioxane: water (1:1, by volume) (20 ml) at 0° C. The reaction mixture was stirred for 20 minutes then benzyl chloroformate (319 mg) was added to the mixture and the solution was stirred for 4 hours. Additional benzyl chloroformate (70 mg) was added to the reaction mixture and it was stirred for a further 1 hour. The solvent was removed under reduced pressure. The resulting solid was dissolved in water and washed with diethyl ether. The aqueous layer was acidified with 2N aqueous hydrochloric acid solution and the product was extracted with ethyl acetate. The organic solution was dried over magnesium sulphate and the solvent removed under reduced pressure to afford 2-[4-(2-[benzyloxycarbonylamino]ethoxy)phenyl]acetic acid (375 mg) as a solid.

Workup

  1. stirringthe solution was stirred for 4 hours
  2. stirringwas stirred for a further 1 hour
  3. customThe solvent was removed under reduced pressure
  4. dissolutionThe resulting solid was dissolved in water
  5. washwashed with diethyl ether
  6. extractionthe product was extracted with ethyl acetate
  7. dry with materialThe organic solution was dried over magnesium sulphate
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-10f89cc941164c239625cc6a8058e8a6
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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