Benzyl Alcohol → HCID 178523855, Verbindung

HRID 516460Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 516460
[CH2:1]([O:3][C:4](=[O:24])[C@H:5]([OH:23])[CH2:6][C@H:7]([NH2:22])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)=[CH:11][CH:10]=1)[CH3:2].C(O)[C:26]1[CH:31]=[CH:30]C=[CH:28][CH:27]=1.Cl.O1CCOCC1.[OH:40][C:41]1[N:45]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=2)[N:44]=[C:43]([C:52]([OH:54])=O)[CH:42]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN(C=O)C.CCN(C(C)C)C(C)C>>[CH2:1]([O:3][C:4](=[O:24])[C@H:5]([OH:23])[CH2:6][C@H:7]([NH:22][C:52]([C:43]1[CH:42]=[C:41]([OH:40])[N:45]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=2)[N:44]=1)=[O:54])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:30]=[CH:31][CH:26]=[CH:27][CH:28]=1

Komponenten

9

Edukt 8

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86682253(2R,4R)-4-amino-5-(3'-chlorobiphenyl-4-yl)-2-hydroxypentanoic acid ethyl esterHCID 178524632HCID 178524632, Verbindung

Produkt 1

HCID 178523855HCID 178523855, VerbindungAusbeute 15,1 %

Versuchsvorschrift

A mixture of (2R,4R)-4-amino-5-(3′-chlorobiphenyl-4-yl)-2-hydroxypentanoic acid ethyl ester (150.0 mg, 431 μmol), benzyl alcohol (446.2 μL, 4.3 mmol), and 4.0 M HCl in 1,4-dioxane (431 μL, 1.7 mmol) was stirred at room temperature overnight, then at 50° C. for 1 hour. The mixture was then concentrated under reduced pressure. 5-Hydroxy-1-pyridin-2-yl-1H-pyrazole-3-carboxylic acid (44.2 mg, 216 μmol) and HATU (98.4 mg, 259 mol) were stirred in DMF (0.5 mL, 5 mmol) for 10 minutes, then added to the concentrated mixture, along with DIPEA (113 μL, 647 μmol). The resulting mixture was stirred at room temperature for 2 hours and concentrated under reduced pressure. The residue was dissolved in 50% AcOH-water (5 mL), filtered, and purified by reverse phase preparative HPLC to yield the title compound (19.5 mg).

Aufarbeitung

  1. waitat 50° C. for 1 hour
  2. concentrationThe mixture was then concentrated under reduced pressure
  3. stirringThe resulting mixture was stirred at room temperature for 2 hours
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in 50% AcOH-water (5 mL)
  6. filtrationfiltered
  7. custompurified by reverse phase preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-78775cbedb4e46aab9267fde71f2c179
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108934B2

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