Acetic Acid → ethyl 3-(3-((((1R,2R,3S,4R)-4-(4-((2,4-dimethoxybenzyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2,3-dihydroxycyclopentyl)methyl)amino)cyclobutyl)propanoate

HRID 511576

Reaktionsgleichung

Reaktionsgleichung von HRID 511576
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:15][CH2:16][C@H:17]1[CH2:21][C@@H:20]([N:22]2[C:26]3[N:27]=[CH:28][N:29]=[C:30]([NH:31][CH2:32][C:33]4[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][C:34]=4[O:41][CH3:42])[C:25]=3[CH:24]=[CH:23]2)[C@H:19]([OH:43])[C@@H:18]1[OH:44].O=[C:46]1[CH2:49][CH:48]([CH2:50][CH2:51][C:52]([O:54][CH2:55][CH3:56])=[O:53])[CH2:47]1.C(O)(=O)C.C([O-])(O)=O.[Na+]>ClCCCl>[CH3:42][O:41][C:34]1[CH:35]=[C:36]([O:39][CH3:40])[CH:37]=[CH:38][C:33]=1[CH2:32][NH:31][C:30]1[C:25]2[CH:24]=[CH:23][N:22]([C@@H:20]3[CH2:21][C@H:17]([CH2:16][NH:15][CH:46]4[CH2:47][CH:48]([CH2:50][CH2:51][C:52]([O:54][CH2:55][CH3:56])=[O:53])[CH2:49]4)[C@@H:18]([OH:44])[C@H:19]3[OH:43])[C:26]=2[N:27]=[CH:28][N:29]=1

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 67775333Ethyl 3-(3-oxocyclobutyl)propanoateHCID 67776960(1S,2R,3R,5R)-3-(aminomethyl)-5-(4-((2,4-dimethoxybenzyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclopentane-1,2-diol

Produkt 1

HCID 67775395ethyl 3-(3-((((1R,2R,3S,4R)-4-(4-((2,4-dimethoxybenzyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2,3-dihydroxycyclopentyl)methyl)amino)cyclobutyl)propanoateAusbeute 55,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

Sodium triacetoxyborohydride (2.43 g, 11.5 mmol) was added to a solution of (1S,2R,3R,5R)-3-(aminomethyl)-5-(4-((2,4-dimethoxybenzyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclopentane-1,2-diol (2.6 g, 5.7 mmol) and ethyl 3-(3-oxocyclobutyl)propanoate (0.976 g, 5.73 mmol) and Acetic acid (0.326 ml, 5.73 mmol) in 1,2-Dichloroethane (20 ml) and reaction was stirred at RT overnight. NaHCO3 was added and the aqueous layer was extracted 3× with DCM. The combined organics were dried with MgSO4, filtered, concentrated and purified by flash chromatogrpahy (DCM/7N NH3 in MeOH 90:10) to give the desired compound (1.8 g) as a thick yellow resin.

Aufarbeitung

  1. extractionthe aqueous layer was extracted 3× with DCM
  2. dry with materialThe combined organics were dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash chromatogrpahy (DCM/7N NH3 in MeOH 90:10)

Quellen und Nachweise

ORD-Eintrag
ord-73962cc6d7264c3ab58f29a99689fef9
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096634B2

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