Bicarbonate Ion → HCID 86761278, compound

HRID 1362906Notes

Reaction equation

HRID 1362906 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH2:14][CH2:13][C@H:12]([C:15]3[CH:20]=[C:19]([F:21])[C:18]([F:22])=[CH:17][C:16]=3[F:23])[C@@H:11]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:10]2)=[N:6][C:7]=1[NH2:8].O=[C:33]([CH3:36])[CH:34]=O.C(=O)(O)[O-]>CO.C(Cl)Cl>[CH3:36][C:33]1[N:8]=[C:7]2[N:6]=[C:5]([N:9]3[CH2:14][CH2:13][C@H:12]([C:15]4[CH:20]=[C:19]([F:21])[C:18]([F:22])=[CH:17][C:16]=4[F:23])[C@@H:11]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:28])([CH3:30])[CH3:29])[CH2:10]3)[CH:4]=[CH:3][C:2]2=[N:1][CH:34]=1

Participants

6

Reactant 3

HCID 769Bicarbonate IonHCID 880MethylglyoxalHCID 86761276HCID 86761276, compound

Product 1

HCID 86761278HCID 86761278, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To 40 mg (0.09 mmol) of the product of Step B in 2 mL of methanol was added 0.07 mL (0.46 mmol) of 2-oxopropanal solution (40 wt. % in water) and stirred at ambient temperature for 1 h. The reaction mixture was then, diluted with 10 mL of methylene chloride and poured into 10 mL of a saturated aqueous bicarbonate solution. The layers were separated and the aqueous layer extracted with three 10 mL portions of methylene chloride and the combined organic phases were dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to yield a tan solid which was purified by preparative thin layer chromatography using an Analtech® 1500 micron plate (1:3 hexane/ethyl acetate solvent) to give the title compound as a tan crystalline solid. LC/MS 474.1 (M+1).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer extracted with three 10 mL portions of methylene chloride
  3. dry with materialthe combined organic phases were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto yield a tan solid which
  7. customwas purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-b22b7dc1a0f8407faea6f2634b465685
Source dataset
uspto-grants-2011_02
Patent number
US07884104B2

Reaction notes

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