Triethylamine → (S)-benzyl 2-(1-(2-(3'-methylbiphenyl-4-yl)-1-(1H-tetrazol-5-yl)ethylcarbamoyl)cyclopentyl)acetate

HRID 333311Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 333311
[CH2:1]([O:8][C:9](=[O:19])[CH2:10][C:11]1([C:16]([OH:18])=O)[CH2:15][CH2:14][CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20]CN=C=NCCCN(C)C.Cl.C1C=NC2N(O)N=NC=2C=1.C(N(CC)CC)C.C[C:50]1[CH:51]=[C:52]([C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)[CH:53]=[CH:54][C:55]=1[CH2:56][C@@H:57]([C:59]1[NH:63][N:62]=[N:61][N:60]=1)[NH2:58]>CN(C=O)C.CCOC(C)=O>[CH3:20][C:68]1[CH:69]=[C:64]([C:52]2[CH:51]=[CH:50][C:55]([CH2:56][C@H:57]([NH:58][C:16]([C:11]3([CH2:10][C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[O:19])[CH2:12][CH2:13][CH2:14][CH2:15]3)=[O:18])[C:59]3[NH:63][N:62]=[N:61][N:60]=3)=[CH:54][CH:53]=2)[CH:65]=[CH:66][CH:67]=1

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 596082261-(2-(Benzyloxy)-2-oxoethyl)cyclopentanecarboxylic acidHCID 178422619HCID 178422619, Verbindung

Produkt 1

HCID 178424508(S)-benzyl 2-(1-(2-(3'-methylbiphenyl-4-yl)-1-(1H-tetrazol-5-yl)ethylcarbamoyl)cyclopentyl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1-(2-(benzyloxy)-2-oxoethyl)cyclopentanecarboxylic acid (150 mg, 0.572 mmol) in DMF (3 mL) were added EDC-HCl (110 mg, 0.572 mmol), HOAt (62.3 mg, 0.423 mmol) and triethylamine (0.133 mL, 0.953 mmol) at room temperature. After being stirred for 0.5 hours, (S)-2-(3-methylbiphenyl-4-yl)-1-(1H-tetrazol-5-yl)ethanamine (106 mg, 0.381 mmol) was added and stirred for 2 hours. The reaction mixture was diluted with EtOAc and washed with saturated NH4Cl aqueous solution and brine. The organic layer was dried over Na2SO4, concentrated under reduced pressure, and purified by silica gel flash column chromatography (10% MeOH in DCM/DCM) to give (S)-benzyl 2-(1-(2-(3′-methylbiphenyl-4-yl)-1-(1H-tetrazol-5-yl)ethylcarbamoyl)cyclopentyl)acetate. LCMS (condition A): 524 (M+1); retention time=1.82 min.

Aufarbeitung

  1. stirringstirred for 2 hours
  2. washwashed with saturated NH4Cl aqueous solution and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. custompurified by silica gel flash column chromatography (10% MeOH in DCM/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-f6c32a3a12634e04b4d04c56ace359bf
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877815B2

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