Ethyl bromopyruvate → HCID 22381051, Verbindung

HRID 895706

Reaktionsgleichung

Reaktionsgleichung von HRID 895706
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[C:3]([SH:6])([CH3:5])[CH3:4].Br[CH2:11][C:12](=O)[C:13]([O:15]CC)=[O:14].C(=O)(O)[O-].[Na+]>O.C(#N)C>[CH3:4][C:3]1([CH3:5])[CH:2]([C:7]([OH:9])=[O:8])[NH:1][C:12]([C:13]([OH:15])=[O:14])=[CH:11][S:6]1

Komponenten

6

Edukt 3

HCID 66144Ethyl bromopyruvateHCID 92863L-PenicillamineHCID 516892Sodium Bicarbonate

Produkt 1

HCID 22381051HCID 22381051, VerbindungAusbeute 34,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of L-penicillamine (298 mg, 2.0 mmol) in water (5 mL) and acetonitrile (5 mL) was added ethyl 3-bromopyruvate (0.25 mL, 390 mg, 2.0 mmol) slowly. To the resulted mixture was added sodium bicarbonate aqueous solution till the pH about 5. Acetonitrile was removed under vacuum and some more water was added. The solution was extracted with methylene chloride. The water phase was separated and freeze-dried under high vacuum. The residue was chromatographed (silica gel, methylene chloride-methanol-acetic acid 100:5:0.3 to 100:10:0.3) to give 150 mg of product (yield 31%). 1HNMR (300 Hz, D3COD) δ (ppm) 6.17 (s, 1H), 4.23 (q, J=7.1 Hz, 2H), 3.79 (s, 1H), 1.48 (s, 3H), 1.31 (t, J=7.1 Hz, 3H), 1.29 (s, 3H). 13CNMR (75 Hz, D3COD) δ (ppm) 173.8, 164.0, 128.0, 102.4, 64.1, 62.2, 41.2, 28.3, 25.2, 14.7 ppm. MS (ESI) m/z 268 (M+Na, 100), 246 (M+1, 5).

Aufarbeitung

  1. customAcetonitrile was removed under vacuum
  2. additionsome more water was added
  3. extractionThe solution was extracted with methylene chloride
  4. customThe water phase was separated
  5. customfreeze-dried under high vacuum
  6. customThe residue was chromatographed (silica gel, methylene chloride-methanol-acetic acid 100:5:0.3 to 100:10:0.3)

Quellen und Nachweise

ORD-Eintrag
ord-cb77d3d769ad426b93264f6323dd9ee8
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06916850B2

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