Glycine → HCID 24780693, compound

HRID 409295Notes

Reaction equation

HRID 409295 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])[S: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])[S: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 2

HCID 750GlycineHCID 67110399HCID 67110399, compound

Product 1

HCID 24780693HCID 24780693, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 1-cyano-4-hydroxy-6-(2-methyl-benzothiazol-6-yloxy)-isoquinoline-3-carboxylic acid butyl ester (113 mg, 0.26 mmol) and glycine (390 mg, 5.20 mmol) in 0.5 M sodium methoxide/methanol (9.9 mL) was refluxed for forty-five hours before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (35 mL) and extracted with methyl tert-butyl ether (2×25 mL). The remaining aqueous layer was acidified to pH=3 with 1N HCl (7.4 mL). The white precipitate was filtered, washed with water and dried in vacuo to give the title compound as a white solid (92 mg): MS: (+) m/z 434.93 (M+1), (−) m/z 432.87 (M−1).

Workup

  1. temperaturewas refluxed for forty-five hours before it
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water (35 mL)
  4. extractionextracted with methyl tert-butyl ether (2×25 mL)
  5. filtrationThe white precipitate was filtered
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-65724072ea9d423c9a157187b334bd16
Source dataset
uspto-grants-2014_06
Patent number
US08759373B2

Reaction notes

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