Glycine → HCID 135870669, compound

HRID 1847219Notes

Reaction equation

HRID 1847219 reaction equation
C(O[C:4]([C:6]1[C:7]([OH:28])=[C:8]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:20][S:19][C:9]2=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[N:11]=1)=[O:5])C.[NH2:29][CH2:30][C:31]([OH:33])=[O:32].C[O-].[Na+]>>[F:18][C:15]1[CH:14]=[CH:13][C:12]([C:10]2[N:11]=[C:6]([C:4]([NH:29][CH2:30][C:31]([OH:33])=[O:32])=[O:5])[C:7]([OH:28])=[C:8]3[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[N:20][S:19][C:9]=23)=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 750GlycineHCID 10942334Sodium MethoxideHCID 136343985HCID 136343985, compound

Product 1

HCID 135870669HCID 135870669, compoundYield 67.5%

Procedure

A mixture of 7-(4-fluoro-phenyl)-4-hydroxy-3-phenyl-isothiazolo[5,4-c]pyridine-5-carboxylic acid ethyl ester (69 mg, 0.175 mmol), glycine (394 mg, 5.25 mmol), and NaOMe (8.75 mL, 4.37 mmol, 0.5 M solution in MeOH) was refluxed for 24 h. After the mixture was cooled to r. t. it was concentrated in vacuo. The residue was dissolved in water (25 mL) and washed with CH2Cl2 (2×15 mL). The aqueous solution was then acidified by addition of aqueous 1N HCl solution. The resulting precipitate was sucked off, washed with water, and dried in vacuo to give the title compound as white solid (50 mg): MS (m/z) 424.2 (M+1).

Workup

  1. temperaturewas refluxed for 24 h
  2. temperatureAfter the mixture was cooled
  3. concentrationit was concentrated in vacuo
  4. dissolutionThe residue was dissolved in water (25 mL)
  5. washwashed with CH2Cl2 (2×15 mL)
  6. additionThe aqueous solution was then acidified by addition of aqueous 1N HCl solution
  7. washwashed with water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-b5b80b2af4d94130ac870c7ee8afe1f4
Source dataset
uspto-grants-2015_02
Patent number
US08952160B2

Reaction notes

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