Cesium carbonate → HCID 68750611, Verbindung

HRID 448211

Reaktionsgleichung

Reaktionsgleichung von HRID 448211
C(=O)([O-])[O-].[Cs+].[Cs+].[C:7]([O:11][C:12]([NH:14][C@@H:15]([C:18]([O:20][CH3:21])=[O:19])[CH2:16]I)=[O:13])([CH3:10])([CH3:9])[CH3:8].[Cl:22][C:23]1[CH:24]=[C:25]([CH2:29][C:30](=[O:32])[CH3:31])[CH:26]=[CH:27][CH:28]=1>CN(C=O)C>[C:7]([O:11][C:12]([NH:14][CH:15]([CH2:16][CH:29]([C:25]1[CH:26]=[CH:27][CH:28]=[C:23]([Cl:22])[CH:24]=1)[C:30](=[O:32])[CH3:31])[C:18]([O:20][CH3:21])=[O:19])=[O:13])([CH3:10])([CH3:9])[CH3:8]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonate2×HCID 27340971-(3-Chlorophenyl)propan-2-oneHCID 11416215(S)-Methyl 2-Boc-amino-3-iodopropionate

Produkt 1

HCID 68750611HCID 68750611, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of cesium carbonate (9.80 g, 30.1 mmol) and methyl N-(tert-butoxycarbonyl)-3-iodo-D-alaninate (9.90 g, 30.1 mmol) in DMF (75 mL) was stirred at 23° C. for 45 min before 1-(3-chlorophenyl)propan-2-one (6.09 g, 36.1 mmol) and additional cesium carbonate (9.80 g, 30.1 mmol) were added. The resulting mixture was stirred for 2.5 h. The majority of the DMF was then removed under reduced pressure at a bath temperature of <40° C. The concentrated mixture was partitioned between water (500 mL) and ethyl acetate (2×200 mL). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated to give the title compound as a 1:1 racemic mixture of diastereomers, which was used without further purification. MS: m/z=314.1 (M-t-Bu+1).

Aufarbeitung

  1. additionwere added
  2. customThe majority of the DMF was then removed under reduced pressure at a bath temperature of <40° C
  3. customThe concentrated mixture was partitioned between water (500 mL) and ethyl acetate (2×200 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-fb9c714847054ac89c96f851bf265097
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481556B2

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