Carbon tetrabromide → Methyl 4-bromo-2-(tert-butoxycarbonylamino)butanoate

HRID 910727Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 910727
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][O:21][C:22](=[O:35])[C@H:23]([CH2:32][CH2:33]O)[NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].C(Br)(Br)(Br)[Br:37]>C(Cl)Cl>[CH3:20][O:21][C:22](=[O:35])[CH:23]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:32][CH2:33][Br:37]

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 10561607Methyl N-(tert-butoxycarbonyl)-L-homoserinate

Produkt 1

HCID 6857808Methyl 4-bromo-2-(tert-butoxycarbonylamino)butanoateAusbeute 20,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of triphenylphosphine (2.20 g, 8.39 mmol) in dry CH2Cl2 (20 mL) was added dropwise via syringe to a solution of N-Boc homoserine methyl ester 29 (8.39 mmol) and carbon tetrabromide (4.18 g, 12.60 mmol) in dry CH2Cl2 (20 mL). The resulting dark solution was stirred at room temperature for 16 h. Hexanes was added and precipitates were removed by suction filtration. The filtrate was concentrated under reduced pressure and subject to flash silica gel column chromatography using ethyl acetate/hexanes (1:10, v/v then 1:6, v/v) to give the desired product 30 as a yellow oil (501 mg, 20% overall yield from homoserine). 1H NMR (300 MHz, CDCl3) δ 1.45 (s, 9H), 2.12-2.48 (m, 2H), 3.39-3.47 (m, 2H), 3.78 (s, 3H), 4.33-4.48 (m, 1H), 5.10-5.22 (m, 1H). m/z (ESI) 296 [C10H18BrNO4+H]+.

Aufarbeitung

  1. customprecipitates
  2. customwere removed by suction filtration
  3. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c61af5a7627b4d099f23b86435e31382
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022210B2

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