N-carbobenzyloxyalanine → [(R)-3-((S)-2-Amino-propionylamino)-2-hydroxy-propyl]-cyclohexylmethyl-phosphinic acid

HRID 1926985

Reaktionsgleichung

Reaktionsgleichung von HRID 1926985
Cl.C([O:9][P:10]([CH2:19][C@H:20]([OH:23])[CH2:21][NH2:22])([CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:11])C1C=CC=CC=1.C([NH:34][C@H:35]([C:37](O)=[O:38])[CH3:36])(OCC1C=CC=CC=1)=O>>[NH2:34][C@@H:35]([CH3:36])[C:37]([NH:22][CH2:21][C@@H:20]([OH:23])[CH2:19][P:10]([CH2:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1)(=[O:11])[OH:9])=[O:38]

Komponenten

3

Edukt 2

HCID 736104N-carbobenzyloxyalanineHCID 68622110((R)-3-amino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid benzyl ester hydrochloride

Produkt 1

HCID 11529614[(R)-3-((S)-2-Amino-propionylamino)-2-hydroxy-propyl]-cyclohexylmethyl-phosphinic acid

Versuchsvorschrift

Step 4, Method B of Example 1 was substantially repeated in this Example 3 except for employing ((R)-3-amino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid benzyl ester hydrochloride and N-Cbz-L-alanine as the starting materials. Subsequent hydrogenation of the resulting benzyl ester in accordance with the procedures of Step 5, Method A of Example 1 and RP-HPLC purification yielded the title compound. 1H NMR (CD3OD, 300 MHz): δ 4.18-3.99 (m, 1H), 3.93 (q, 1H), 3.42-3.25 (m, 2H), 1.98-1.85 (m, 2H), 1.83-1.61 (m, 6H), 1.59-1.55 (m, 2H), 1.52 (d, 3H), 1.42-0.98 (m, 5H). 31P NMR (CD3OD, 300 MHz): δ 42.98. LCMS m/z: [M+H]+=307.2.

Aufarbeitung

  1. customSubsequent hydrogenation of the resulting benzyl ester in accordance with the procedures of Step 5, Method A of Example 1 and RP-HPLC purification

Quellen und Nachweise

ORD-Eintrag
ord-07a8ef73c5764432ae5a2589f1d6965c
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183231B2

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