Lithium Hydroxide → 3-(Dipropylcarbamoyl)benzoic acid

HRID 20946

Reaktionsgleichung

Reaktionsgleichung von HRID 20946
F[C:2]1[CH:3]=C(C=C(F)[CH:42]=1)C[C@H](C(N1[C@@H](CC2C=CC=CC=2)COC1=O)=O)[C@@H]([C@H]1C[C@@H](OCC=C)CN1C(OC(C)(C)C)=O)O.C(OC(N1C[C@H](OCCC)C[C@@H]1[C@@H](O[Si](C(C)(C)C)(C)C)[C@@H:61]([NH:71][C:72]([C:74]1[CH:75]=[C:76]([CH:80]=[C:81](C)[CH:82]=1)[C:77]([OH:79])=[O:78])=[O:73])[CH2:62][C:63]1C=C(F)C=C(F)C=1)=O)(C)(C)C.[Si](O[C@H]([C@H]1C[C@@H](OCCC)CN1C(OC(C)(C)C)=O)[C@@H](NC(=O)C1C=C(C)C=C(C(OC)=O)C=1)CC1C=C(F)C=C(F)C=1)(C(C)(C)C)(C)C.[Li+].[OH-]>C1COCC1.O.C(OCC)C.CO>[CH2:42]([N:71]([CH2:61][CH2:62][CH3:63])[C:72]([C:74]1[CH:75]=[C:76]([CH:80]=[CH:81][CH:82]=1)[C:77]([OH:79])=[O:78])=[O:73])[CH2:2][CH3:3]

Komponenten

9

Edukt 4

HCID 3939Lithium HydroxideHCID 593468483-(((1S,2S)-1-((2R,4R)-1-(tert-butoxycarbonyl)-4-propoxypyrrolidin-2-yl)-1-(tert-butyldimethylsilyloxy)-3-(3,5-difluorophenyl)propan-2-yl)carbamoyl)-5-methylbenzoic acidHCID 67316204(2R,4R)-tert-butyl 2-((1S,2S)-1-(tert-butyldimethylsilyloxy)-3-(3,5-difluorophenyl)-2-(3-(methoxycarbonyl)-5-methylbenzamido)propyl)-4-propoxypyrrolidine-1-carboxylateHCID 67316359(2R,4R)-tert-butyl 2-((1S,2S)-2-(3,5-difluorobenzyl)-3-((S)-4-benzyl-2-oxooxazolidin-3-yl)-1-hydroxy-3-oxopropyl)-4-(allyloxy)pyrrolidine-1-carboxylate

Produkt 1

HCID 1827693-(Dipropylcarbamoyl)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Step G (5): Preparation of 3-(((1S,2S)-1-((2R,4R)-1-(tert-butoxycarbonyl)-4-propoxypyrrolidin-2-yl)-1-(tert-butyldimethylsilyloxy)-3-(3,5-difluorophenyl)propan-2-yl)carbamoyl)-5-methylbenzoic acid. To a solution of (2R,4R)-tert-butyl 2-((1S,2S)-1-(tert-butyldimethylsilyloxy)-3-(3,5-difluorophenyl)-2-(3-(methoxycarbonyl)-5-methylbenzamido)propyl)-4-propoxypyrrolidine-1-carboxylate (Step G (4), 110 mg, 0.16 mmol) in THF (2 mL) was added a solution of LiOH (18 mg, 0.8 mmol) in H2O (0.4 mL). This reaction mixture was stirred at rt for 2 h. MeOH (2 mL) was added to the reaction mixture and stirred for another 2 h at rt. Ethyl ether (100 mL) was added to the mixture and washed with 1N HCl, H2O, dried (Na2SO4), and concentrated in vacuo to give 105 mg of the title compound: 1H NMR (CDCl3, 500 MHz) δ ppm 0.05 (3H, s), 0.10 (3H, s), 0.93 (3H, m), 0.97 (9H, s), 1.47 (9H, s), 1.58 (2H, m), 2.26 (1H, m), 2.39 (3H, s), 2.47-2.52 (1H, m), 2.61 (1H, m), 3.07 (1H, m), 3.27 (1H, m), 3.37 (1H, dt, J=5, 10 Hz), 3.47 (1H, dt, J=5, 10 Hz), 3.86 (1H, dd, J=5, 10 Hz), 3.97 (1H, m), 4.12 (1H, m), 4.36 (1H, m), 4.50 (1H, m), 6.47 (1H, m), 6.89 (1H, s), 6.90 (1H, s), 7.90 (1H, s), 7.95 (1H, s), 8.26 (1H, d, J=10 Hz), 8.54 (1H, s). MS (ESI) (M−H)− 689.49.

Aufarbeitung

  1. stirringstirred for another 2 h at rt
  2. washwashed with 1N HCl, H2O
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fe7e12d7e5ab4023bac4ff900b153e5d
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745470B2

Verknüpfte Notizen

Wird geladen…