HCID 67506102, Verbindung → (2R,4S)-5-(3'-Chloro-biphenyl-4-yl)-2-methyl-4-[(2H-tetrazole-5-carbonyl)-amino]-pentanoic acid ethyl ester

HRID 1469628Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1469628
[CH2:1]([O:3][C:4](=[O:40])[C@@H:5]([CH3:39])[CH2:6][CH:7]([NH:22][C:23]([C:25]1[N:26]=[N:27][N:28](CC2C=CC(OC)=CC=2)[N:29]=1)=[O:24])[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(F)(F)F)=O>[CH2:1]([O:3][C:4](=[O:40])[C@H:5]([CH3:39])[CH2:6][C@H:7]([NH:22][C:23]([C:25]1[N:29]=[N:28][NH:27][N:26]=1)=[O:24])[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)=[CH:13][CH:14]=1)[CH3:2]

Komponenten

3

Edukt 1

HCID 67506102HCID 67506102, Verbindung

Produkt 1

HCID 59608348(2R,4S)-5-(3'-Chloro-biphenyl-4-yl)-2-methyl-4-[(2H-tetrazole-5-carbonyl)-amino]-pentanoic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

Next, a solution of (S)-5-(3′-chloro-biphenyl-4-yl)-4-{[2-(4-methoxy-benzyl)-2H-tetrazole-5-carbonyl]-amino}-2-methyl-pentanoic acid ethyl ester (212 mg, 0.377 mmol) in TFA (5 mL) is stirred at room temperature for 18 hours. The solvent is removed under reduced pressure and the residue is purified by chiral HPLC on a Chirapak IA column using heptane/ethanol (80:20) (0.1% TFA) to elute the title compound; HPLC Retention time 1.59 minutes (condition C): MS 442.2 (M+1); 1 H NMR (400 MHz, DMSO-d6) δ ppm 1.05-1.10 (m, 3 H) 1.10-1.16 (m, 3 H) 1.69-1.79 (m, 1 H) 1.88 (ddd, J=13.89, 9.98, 3.92 Hz, 1 H) 2.77-2.87 (m, 1 H) 2.87-2.96 (m, 1 H) 3.91-4.05 (m, J=10.72, 7.14, 7.14, 3.66, 3.66 Hz, 2 H) 4.24 (br. s., 1 H) 6.85-6.85 (m, 0 H) 7.30 (d, J=8.34 Hz, 2 H) 7.37-7.42 (m, 1 H) 7.46 (t, J=7.83 Hz, 1 H) 7.56-7.64 (m, 3 H) 7.68 (t, J=1.77 Hz, 1 H) 9.18 (br. s., 1 H).

Aufarbeitung

  1. customThe solvent is removed under reduced pressure
  2. customthe residue is purified by chiral HPLC on a Chirapak IA column
  3. washto elute the title compound

Quellen und Nachweise

ORD-Eintrag
ord-934ae7874bae4656a99275459e62e724
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006249B2

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