D-Alanine → HCID 135870685, compound

HRID 1847246Notes

Reaction equation

HRID 1847246 reaction equation
C(O[C:4]([C:6]1[C:7]([OH:22])=[C:8]2[C:14]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)=[N:13][S:12][C:9]2=[CH:10][N:11]=1)=[O:5])C.[NH2:23][C@@H:24]([C:26]([OH:28])=[O:27])[CH3:25].C[O-].[Na+]>>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([C:14]2[C:8]3[C:9](=[CH:10][N:11]=[C:6]([C:4]([NH:23][C@H:24]([CH3:25])[C:26]([OH:28])=[O:27])=[O:5])[C:7]=3[OH:22])[S:12][N:13]=2)=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 71080D-AlanineHCID 10942334Sodium MethoxideHCID 136344064HCID 136344064, compound

Product 1

HCID 135870685HCID 135870685, compoundYield 69.6%

Procedure

A mixture of 3-(4-Chloro-phenyl)-4-hydroxy-isothiazolo[5,4-c]pyridine-5-carboxylic acid ethyl ester (50 mg, 0.149 mmol), D-alanine (400 mg, 4.49 mmol) and NaOMe (7.45 mL, 3.72 mmol, 0.5 M solution in MeOH) was refluxed for 48 h before it was concentrated in vacuo. The residue was dissolved in water (50 mL) and washed with CH2Cl2 (2×20 mL). The aqueous solution was then acidified by addition of 1N HCl solution. The resulting precipitate was sucked off, washed with water, and dried in vacuo to give the title compound as a white solid (39.2 mg): MS (m/z) 376.0 (M−1).

Workup

  1. temperaturewas refluxed for 48 h before it
  2. concentrationwas concentrated in vacuo
  3. dissolutionThe residue was dissolved in water (50 mL)
  4. washwashed with CH2Cl2 (2×20 mL)
  5. additionThe aqueous solution was then acidified by addition of 1N HCl solution
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-257f71f9cef04f30b6a5f9cb1bedaafc
Source dataset
uspto-grants-2015_02
Patent number
US08952160B2

Reaction notes

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