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Triethylamine → Br-Boc-C2-azido

HRID 876072
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 876072
[N:1]([CH2:4][CH2:5][OH:6])=[N+:2]=[N-:3].CCN(CC)CC.[Br:14][C:15]([CH3:20])([CH3:19])[C:16](Br)=[O:17]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[N:1]([CH2:4][CH2:5][O:6][C:16](=[O:17])[C:15]([Br:14])([CH3:20])[CH3:19])=[N+:2]=[N-:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8471Triethylamine2×HCID 886852-Bromo-2-methylpropionyl bromideHCID 1231182-Azidoethanol

Produkt 1

HCID 86650124Br-Boc-C2-azido

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344
Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

2-Azidoethanol (17.40 g, 0.2 mol), freshly distilled methylene chloride (150 mL), and Et3N (21.21 g, 0.21 mol) were added into a three-neck round-bottom flask equipped with a condenser and a dropping funnel. Under nitrogen atmosphere and magnetic stirring, freshly distilled anhydrous methylene chloride (150 mL), DMAP (1.7 g, 14 mmol), and freshly distilled anhydrous Et3N (46.5 g, 0.46 mol) were sequentially added. After the flask was immersed into an ice-water bath, 2-bromoisobutyryl bromide (48.28 g, 0.21 mol) was added dropwise into the previous solution. Twenty-four hours later, the reaction mixture was washed successively with 1M HCl (3×200 mL) solution and deionized water (1×200 mL). The organic phase was dried over anhydrous MgSO4 overnight. After filter and removal of methylene chloride on a rotary evaporator, the obtained residues were distilled under reduced pressure to give a colorless viscous liquid. The yield was: 33.4 g, 70%. 1H NMR (CDCl3, δ, ppm): 4.24 (t, 2H, N3CH2CH2), 3.52 (t, 2H, N3CH2), 1.96 (s, 6H, (CH3)2Br).

Aufarbeitung

  1. customequipped with a condenser and a dropping funnel
  2. customAfter the flask was immersed into an ice-water bath
  3. washTwenty-four hours later, the reaction mixture was washed successively with 1M HCl (3×200 mL) solution
  4. dry with materialThe organic phase was dried over anhydrous MgSO4 overnight
  5. filtrationAfter filter
  6. customremoval of methylene chloride
  7. customon a rotary evaporator
  8. distillationthe obtained residues were distilled under reduced pressure
  9. customto give a colorless viscous liquid

Quellen und Nachweise

ORD-Eintrag
ord-d3d9a2e3a2c04423b59825ac53d54c09
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08986512B2

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