Citric Acid → HCID 71187264, compound

HRID 2402565Notes

Reaction equation

HRID 2402565 reaction equation
O.[OH-].[Li+].C1COCC1.[CH3:9][C:10]([NH:16][C:17]1[CH:22]=[CH:21][N:20]=[C:19]([C:23]2[C:31]3[C:26](=[N:27][CH:28]=[CH:29][CH:30]=3)[N:25](S(C3C=CC(C)=CC=3)(=O)=O)[CH:24]=2)[N:18]=1)([CH2:14][CH3:15])[C:11]([O-:13])=[O:12].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O>[NH:25]1[C:26]2=[N:27][CH:28]=[CH:29][CH:30]=[C:31]2[C:23]([C:19]2[N:18]=[C:17]([NH:16][C:10]([CH3:9])([CH2:14][CH3:15])[C:11]([OH:13])=[O:12])[CH:22]=[CH:21][N:20]=2)=[CH:24]1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 86682098HCID 86682098, compound

Product 1

HCID 71187264HCID 71187264, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Lithium hydroxide hydrate (1.9 g, 45 mmol) was added to 50 mL THF and 15 mL water. Then 2-methyl-2-((2-(1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)amino)butanoate was added and the mixture was heated to reflux for 18 hours. The reaction was cooled to rt and 50 mL 1M citric acid solution was added. The mixture was extracted with 3×100 mL ethyl acetate where upon a white precipitate formed in the aqueous layer. The product was then filtered from the aqueous layer and dried under vacuum affording 1.6 g (68%) 2-((2-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)amino)-2-methylbutanoic acid as white solid. 1H NMR (300 MHz, MeOD) 8.87 (dd, 1H), 8.32 (m, 2H), 7.94 (d, 1H), 3.31 (m, 3H), 2.80 (q, 1H), 2.29-1.95 (m, 2H), 1.68 (s, 3H), 0.96 (t, 3H). m/e m+1=312.22.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 18 hours
  3. extractionThe mixture was extracted with 3×100 mL ethyl acetate where upon a white precipitate
  4. customformed in the aqueous layer
  5. filtrationThe product was then filtered from the aqueous layer
  6. customdried under vacuum

Sources & evidence

ORD record
ord-2d2b7a3fc94245bc8c8a3d29a6e75150
Source dataset
uspto-grants-2014_08
Patent number
US08796453B2

Reaction notes

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