N-Cbz-d-alanine → [(R)-3-((R)-2-Amino-propionylamino)-2-hydroxy-propyl]-cyclohexylmethyl-phosphinic acid

HRID 72164

Reaktionsgleichung

Reaktionsgleichung von HRID 72164
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 70832N-Cbz-d-alanineHCID 68622110((R)-3-amino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid benzyl ester hydrochloride

Produkt 1

HCID 11673928[(R)-3-((R)-2-Amino-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 B and employing ((R)-3-amino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid benzyl ester hydrochloride and N-Cbz-D-alanine 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 4.04 (m, 1H), 3.89 (q, J=6.9 Hz, 1H,), 3.39 (dd, J=5.7, 13.5, 1H), 3.23 (dd, J=5.4, 13.5 Hz, 1H,), 1.85 (m, 2H), 1.77-1.62 (m, 6H), 1.57-1.53 (m, 2H), 1.48 (d, J=6.9 Hz, 3H), 1.37-1.15 (m, 3H), 1.08-0.97 (m, 2H). 31P NMR (CD3OD, 300 MHz): δ 43.74. LCMS m/z: [M+H]+=307.2.

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-4ca6465e66e94b36b82c1e656faa2ced
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828974B2

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