Benzyloxycarbonylglycine → [(R)-3-(2-Amino-acetylamino)-2-hydroxy-propyl]-cyclohexylmethyl-phosphinic acid

HRID 72150

Reaktionsgleichung

Reaktionsgleichung von HRID 72150
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][CH2:35][C:36](O)=[O:37])(OCC1C=CC=CC=1)=O>>[NH2:34][CH2:35][C:36]([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:37]

Komponenten

3

Edukt 2

HCID 14349BenzyloxycarbonylglycineHCID 68622110((R)-3-amino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid benzyl ester hydrochloride

Produkt 1

HCID 11587384[(R)-3-(2-Amino-acetylamino)-2-hydroxy-propyl]-cyclohexylmethyl-phosphinic acid

Versuchsvorschrift

Step 4, Method B of Example 1 was substantially repeated in this Example 2 except for employing ((R)-3-amino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid benzyl ester hydrochloride and N-Cbz-glycine as the starting materials. Subsequent hydrogenation of the resulting benzyl ester in accordance with the procedures of Step 5, Method A of Example 1 yielded the title compound. 1H NMR (CD3OD, 300 MHz): δ 4.18-4.01 (m, 1H), 3.85 (s, 2H), 3.55-3.40 (m, 1H), 3.38-3.22 (m, 1H), 1.91-1.40 (m, 10H), 1.38-0.90 (m, 5H). 31P NMR (CD3OD, 300 MHz): δ 39.92. LCMS m/z: [M+H]+=293.1.

Quellen und Nachweise

ORD-Eintrag
ord-84ee7b95d41e4231a34c13fb1b2c48d4
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828974B2

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