(R)-1-Phenylpropylamine → (R)-1-(benzyloxycarbonylamino)-2-methylpropylphosphonous acid

HRID 1677608

Reaktionsgleichung

Reaktionsgleichung von HRID 1677608
[CH2:1]([O:8][C:9]([NH:11][CH:12]([P:16]([OH:18])[OH:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[C@@H](N)C1C=CC=CC=1>C(O)C.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([P:16]([OH:17])[OH:18])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 5324978(R)-1-PhenylpropylamineHCID 213258521-Carbobenzyloxyamino-2-methylpropanephosphonous acid

Produkt 1

HCID 67375324(R)-1-(benzyloxycarbonylamino)-2-methylpropylphosphonous acidAusbeute 32,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 1-(benzyloxycarbonylamino)-2-methylpropylphosphonous acid (3.4 g, 12.5 mmol) in 20 mL of absolute ethanol was heated to reflux and (R)-(+)-methylbenzylamine (96% ee, 1.5 g, 12.5 mmol) was added. The resulting mixture was diluted with 120 mL of ethyl acetate. The precipitate was filtered off, washed with 100 mL of ethyl acetate and 100 mL of ether, dried in vacuo to afford (R)-1-(benzyloxycarbonylamino)-2-methylpropylphosphonous acid as a white solid (1.1 g) with a rotation [α]D=−10.87° (c=10 mg/mL 9:1 DMF-H2O). This material was found to be 93% ee by chiral HPLC.

Aufarbeitung

  1. temperatureto reflux
  2. filtrationThe precipitate was filtered off
  3. washwashed with 100 mL of ethyl acetate and 100 mL of ether
  4. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6ea9d939b9b74e04a2d660d2ee438185
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008325B2

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