N-benzyloxycarbonyl-l-tyrosine → {(r)-3-[(s)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-2-hydroxy-propyl}-cyclohexylmethyl-phosphinic acid

HRID 72166

Reaktionsgleichung

Reaktionsgleichung von HRID 72166
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.C1C=CC(COC([NH:34][C@H:35]([C:44](O)=[O:45])[CH2:36][C:37]2[CH:42]=[CH:41][C:40]([OH:43])=[CH:39][CH:38]=2)=O)=CC=1>>[NH2:34][C@@H:35]([CH2:36][C:37]1[CH:42]=[CH:41][C:40]([OH:43])=[CH:39][CH:38]=1)[C:44]([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:45]

Komponenten

3

Edukt 2

HCID 712438N-benzyloxycarbonyl-l-tyrosineHCID 68622110((R)-3-amino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid benzyl ester hydrochloride

Produkt 1

HCID 11538543{(r)-3-[(s)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-2-hydroxy-propyl}-cyclohexylmethyl-phosphinic acid

Versuchsvorschrift

The title compound was prepared substantially following the procedures as set forth in Step 4, Example 1, Method A, and employing ((R)-3-Amino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid benzyl ester hydrochloride and N-Cbz-L-tyrosine-OH as the starting materials. Subsequent hydrogenation of the resulting product in accordance with the procedures of Step 5, Example 1, Method B, and RP-HPLC purification yielded the title compound. 1H NMR (CD3OD, 300 MHz): δ 7.11 (d, 2H), 6.78 (d, 2H), 4.14-3.86 (m, 2H), 3.40 (dd, 1H), 3.22-3.03 (m, 2H), 3.01-2.88 (m, 1H), 1.94 (br.d, 2H), 1.86-1.58 (m, 6H), 1.51 (dd, 2H), 1.40-1.13 (m, 3H), 1.11-0.93 (m, 2H). 31P NMR (CD3OD, 300 MHz): δ 40.19. LCMS m/z: [M+H]+=399.3.

Aufarbeitung

  1. customThe title compound was prepared substantially
  2. customSubsequent hydrogenation of the resulting product in accordance with the procedures of Step 5, Example 1, Method B, and RP-HPLC purification

Quellen und Nachweise

ORD-Eintrag
ord-1b6ea89706934443ac8a7043d55e2501
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828974B2

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