N-alpha-Benzyloxycarbonyl-D-valine → [(R)-3-((R)-2-Amino-3-methyl-butyrylamino)-2-hydroxy-propyl]-cyclohexylmethyl-phosphinic acid

HRID 72152

Reaktionsgleichung

Reaktionsgleichung von HRID 72152
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:39](O)=[O:40])[CH:36]([CH3:38])[CH3:37])(OCC1C=CC=CC=1)=O>>[NH2:34][C@H:35]([CH:36]([CH3:38])[CH3:37])[C:39]([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:40]

Komponenten

3

Edukt 2

HCID 712434N-alpha-Benzyloxycarbonyl-D-valineHCID 68622110((R)-3-amino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid benzyl ester hydrochloride

Produkt 1

HCID 11573547[(R)-3-((R)-2-Amino-3-methyl-butyrylamino)-2-hydroxy-propyl]-cyclohexylmethyl-phosphinic acid

Versuchsvorschrift

Step 4, Method B of Example 1 was substantially repeated in this Example 4 except for employing ((R)-3-amino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid benzyl ester hydrochloride and N-Cbz-D-valine 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 4.15-4.01 (m, 1H), 3.58 (d, 1H), 3.55-3.43 (m, 1H), 3.32-3.15 (m, 1H), 2.25-2.07 (m, 1H), 2.02-1.85 (m, 2H), 1.83-1.58 (m, 6H), 1.56-1.45 (m, 2H), 1.42-1.18 (m, 3H), 1.10 (d, 6H), 1.08-0.96 (m, 2H). 31P NMR (CD3OD, 300 MHz): δ 40.91. LCMS m/z: [M+H]+=335.1.

Quellen und Nachweise

ORD-Eintrag
ord-df1312fadb1e463eada49a39a6f18411
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828974B2

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