Dicyclohexylcarbodiimide → S-[(Diphenylphosphino)methyl] 2-(acetylamino)ethanethioate

HRID 488898Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 488898
[C:1]([NH:4][CH2:5][C:6]([OH:8])=O)(=[O:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.[C:34]1([P:40]([CH2:47][SH:48])[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CN(C=O)C.C(OCC)(=O)C>[C:34]1([P:40]([CH2:47][S:48][C:6](=[O:8])[CH2:5][NH:4][C:1](=[O:3])[CH3:2])[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Komponenten

7

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 10972AcetylglycineHCID 757711-HydroxybenzotriazoleHCID 11230015(DIPHENYLPHOSPHINO)METHANETHIOL

Produkt 1

HCID 11359470S-[(Diphenylphosphino)methyl] 2-(acetylamino)ethanethioateAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

N-Acetylglycine (1.90 g, 16.2 mmol) was dissolved in anhydrous DMF (75 mL). HOBt (2.48 g, 16.2 mmol) was added to the resulting solution followed by DCC (3.34 g, 16.2 mmol). Once precipitate (DCU) was observed, phosphinothiol 1b was added (3.77 g, 16.2 mmol). The reaction mixture was allowed to stir under Ar(g) for 3 h. The precipitate was removed by filtration, and the filtrate was concentrated under reduced pressure to give a white solid. This solid was dissolved in ethyl acetate and purified by flash chromatography (silica gel, ethyl acetate). Compound 51 was isolated in 96% yield. Spectral Data. As reported previously.4b

Aufarbeitung

  1. customThe precipitate was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto give a white solid
  4. custompurified by flash chromatography (silica gel, ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-43b5f5a56f494c5dac84abbadfed98ce
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06974884B2

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