Glycine → HCID 24780836, compound

HRID 409319Notes

Reaction equation

HRID 409319 reaction equation
C(O[C:6]([C:8]1[N:9]=[C:10]([C:30]#[N:31])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([O:19][C:20]1[CH:29]=[CH:28][C:23]3[N:24]=[C:25]([CH3:27])[O:26][C:22]=3[CH:21]=1)=[CH:13][CH:12]=2)=[O:7])CCC.[NH2:32][CH2:33][C:34]([OH:36])=[O:35].C[O-].[Na+].CO>>[C:30]([C:10]1[C:11]2[C:16](=[CH:15][C:14]([O:19][C:20]3[CH:29]=[CH:28][C:23]4[N:24]=[C:25]([CH3:27])[O:26][C:22]=4[CH:21]=3)=[CH:13][CH:12]=2)[C:17]([OH:18])=[C:8]([C:6]([NH:32][CH2:33][C:34]([OH:36])=[O:35])=[O:7])[N:9]=1)#[N:31]

Participants

4

Reactant 3

HCID 750GlycineHCID 23694274Sodium methanolate methanolHCID 67110145HCID 67110145, compound

Product 1

HCID 24780836HCID 24780836, compoundYield 90.6%

Procedure

A mixture of 1-cyano-4-hydroxy-6-(2-methyl-benzooxazol-6-yloxy)-isoquinoline-3-carboxylic acid butyl ester (81 mg, 0.19 mmol), glycine (292 mg, 3.89 mmol), and 0.5 M sodium methoxide/methanol (7.4 mL) was refluxed for twenty-six hours before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (25 mL) and extracted with dichloromethane (2×35 mL). The remaining aqueous layer was acidified to pH=3 with 1N HCl (5.5 mL). The precipitate was filtered, washed with water and dried in vacuo to give the title compound as a brown solid (72 mg): MS: (+) m/z 419.30 (M+1); (−) m/z 417.28 (M−1).

Workup

  1. temperaturewas refluxed for twenty-six hours before it
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water (25 mL)
  4. extractionextracted with dichloromethane (2×35 mL)
  5. filtrationThe precipitate was filtered
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-04266e1810cc42efb07ea99528b2f72b
Source dataset
uspto-grants-2014_06
Patent number
US08759373B2

Reaction notes

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