Lithium Hydroxide → HCID 178524247, compound

HRID 523376Notes

Reaction equation

HRID 523376 reaction equation
C[O:2][C:3]([C:5]1[C:13]2[NH:12][C:11]([C:14]3[C:15](=[O:30])[NH:16][CH:17]=[CH:18][C:19]=3[NH:20][CH2:21][C@@H:22]([OH:29])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].[Li+].[OH-].C1COCC1>O>[OH:29][C@@H:22]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:21][NH:20][C:19]1[CH:18]=[CH:17][NH:16][C:15](=[O:30])[C:14]=1[C:11]1[NH:12][C:13]2[C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]=[CH:8][C:9]=2[N:10]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 178497576HCID 178497576, compound

Product 1

HCID 178524247HCID 178524247, compoundYield 102.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

In a 200 mL round-bottomed flask, 2-[4-((S)-2-hydroxy-2-phenyl-ethylamino)-2-oxo-1,2-dihydro-pyridin-3-yl]-3H-benzoimidazole-4-carboxylic acid methyl ester (0.87 g, 2.15 mmol) and LiOH (258 mg, 10.8 mmol) were combined with THF (20 mL1) and Water (5 mL) to give a purple suspension. The reaction was stirred at room temperature overnight. The next day the reaction was heated in dry block at 50° C. for 3.5 hr and cooled to room temperature. The reaction was dilute with water, concentrated, dilute with more water, and acidify with 1M HCl, and filtered. The resulting solid was washed with water and hexanes, and dried over house vacuum yielding 2-[4-((S)-2-hydroxy-2-phenyl-ethylamino)-2-oxo-1,2-dihydro-pyridin-3-yl]-3H-benzoimidazole-4-carboxylic acid (0.86 g, 102% yield) as a purple solid. LC/MS calcd for C21H18N4O4 (m/e) 390.0, obsd 391.2 (M+H); 1H NMR; (DMSO-d6) δ: 13.35 (s, 1H), 11.19 (d, J=6.0 Hz, 1H), 10.97 (t, J=4.9 Hz, 1H), 7.75 (dd, J=7.7, 3.9 Hz, 2H), 7.56 (d, J=7.3 Hz, 2H), 7.22-7.44 (m, 5H), 6.20 (d, J=7.5 Hz, 1H), 5.80 (br. s., 1H), 4.92 (t, J=5.5 Hz, 1H), 3.54-3.74 (m, 3H).

Workup

  1. customto give a purple suspension
  2. temperatureThe next day the reaction was heated in dry block at 50° C. for 3.5 hr
  3. temperaturecooled to room temperature
  4. concentrationconcentrated
  5. additiondilute with more water
  6. filtrationfiltered
  7. washThe resulting solid was washed with water and hexanes
  8. customdried over house vacuum

Sources & evidence

ORD record
ord-7d4fd32f5c4e49fd95b6fcf01f12f2d3
Source dataset
uspto-grants-2016_05
Patent number
US09334480B2

Reaction notes

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