Carbon tetrabromide → N-Boc-beta-bromoalanine benzyl ester

HRID 2217144

Reaktionsgleichung

Reaktionsgleichung von HRID 2217144
[CH2:1]([O:8][C:9](=[O:21])[C@H:10]([CH2:19]O)[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Br)(Br)(Br)[Br:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH2:1]([O:8][C:9](=[O:21])[C@H:10]([CH2:19][Br:23])[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 7018792Boc-Ser-OBzl

Produkt 1

HCID 11772725N-Boc-beta-bromoalanine benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The N-Boc-serine benzyl ester was brought up in dichloromethane (170 mL) and treated with carbon tetrabromide (26.37 g, 79.51 mmol, 1.2 eq.), and triphenylphosphine (25.20 g, 96.08 mmol, 1.45 eq.) and the solution was stirred at 0° C. for 30 min. The volatiles were then evaporated in vacuo and the residue was triturated with ether (1000 mL). The solid that separated out was filtered off and organic layer was evaporated in vacuo to get the crude product. The crude material was purified by flash chromatography on silica gel to get N-Boc-β-bromoalanine benzyl ester.

Aufarbeitung

  1. customThe volatiles were then evaporated in vacuo
  2. customthe residue was triturated with ether (1000 mL)
  3. customThe solid that separated out
  4. filtrationwas filtered off
  5. customorganic layer was evaporated in vacuo
  6. customto get the crude product
  7. customThe crude material was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-e5969927f6bd48ac9c7051628377c1da
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07407952B2

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