Hydrochloric Acid → N-(Bromoacetyl)glycine

HRID 27209

Reaktionsgleichung

Reaktionsgleichung von HRID 27209
[NH2:1][CH2:2][C:3]([O:5]C(C)(C)C)=[O:4].N1C=CC=CC=1.[Br:16][CH2:17][C:18](Br)=[O:19].Cl>C(Cl)Cl>[Br:16][CH2:17][C:18]([NH:1][CH2:2][C:3]([OH:5])=[O:4])=[O:19]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 61147Bromoacetyl bromideHCID 151417Glycine tert-butyl ester

Produkt 1

HCID 12908896N-(Bromoacetyl)glycineAusbeute 153,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 4 g (0.02 mol) of t-butyl glycinate and 4 ml of pyridine in 100 ml of methylene dichloride at 0° under nitrogen was added a solution of 2.01 ml (0.024 mol) of bromoacetyl bromide in 10 ml of methylene dichloride. After the addition, the mixture was stirred for 3 hrs and poured into 1 N aqueous hydrochloride. The organic layer was separated and then washed successively with 1 N HCl, water and brine. After drying over anhydrous sodium sulfate, the mixture was evaporated to dryness in vacuo to yield 6 g of a light brown product, which upon recrystallization from hexane-ethyl acetate, yielded a product with mp 90°-91°.

Aufarbeitung

  1. additionAfter the addition
  2. customThe organic layer was separated
  3. washwashed successively with 1 N HCl, water and brine
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. customthe mixture was evaporated to dryness in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-125ab11c42e04c898d0f4e5a564a0e20
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04220722

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