Triethylamine → (S)-4-(Benzyloxycarbonyl)-1-(diphenylacetyl)piperazine-2-carboxylic acid

HRID 486747Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 486747
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][C@H:13]([C:17]([OH:19])=[O:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:27]1([CH:33]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:34](Cl)=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:34](=[O:35])[CH:33]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C@H:13]([C:17]([OH:19])=[O:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 746372,2-Diphenylacetyl chlorideHCID 1514273(S)-4-(Benzyloxycarbonyl)piperazine-2-carboxylic acid

Produkt 1

HCID 22850671(S)-4-(Benzyloxycarbonyl)-1-(diphenylacetyl)piperazine-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 1.00 g (3.78 mmole) of (S)-4-(benzyloxycarbonyl)piperazine-2-carboxylic acid (from Example 7, Step A) in 10 ml of DMF at 25° C. was treated with 0.755 g. (7.46 mmole) of triethylamine. The solution was cooled to 0° C. and 0.95 g (4.12 mmole) of diphenylacetyl chloride was added in Portions over 2 hours. The solution was stirred at 25° C. for 64 hours, concentrated in vacuo and partitioned between 60 ml. of 1N HCl and 60 ml of ethyl acetate. The ethyl acetate was dried over sodium sulfate, concentrated in vacuo and chromatographed in two portions over an 85×2.5 cm LH-20 column with 11 ml fractions of methanol. Fractions 38-41 from both columns were combined and concentrated in vacuo to 785 mg (44%) of oil which was homogeneous by TLC (80:20:2 chloroform-methanol-ammonia water, Rf =0.40).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. custompartitioned between 60 ml
  3. dry with materialThe ethyl acetate was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customchromatographed in two portions over an 85×2.5 cm
  6. concentrationconcentrated in vacuo to 785 mg (44%) of oil which

Quellen und Nachweise

ORD-Eintrag
ord-676822223e0e4b51828763b5804e2edf
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05292726

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