Glycine → HCID 135870681, compound

HRID 1050771Notes

Reaction equation

HRID 1050771 reaction equation
C(O[C:4]([C:6]1[C:7]([OH:28])=[C:8]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)=[N:19][S:18][C:9]2=[C:10]([C:12]#[C:13][Si](C)(C)C)[N:11]=1)=[O:5])C.[NH2:29][CH2:30][C:31]([OH:33])=[O:32].C[O-].[Na+]>>[Cl:27][C:24]1[CH:23]=[CH:22][C:21]([C:20]2[C:8]3[C:9](=[C:10]([C:12]#[CH:13])[N:11]=[C:6]([C:4]([NH:29][CH2:30][C:31]([OH:33])=[O:32])=[O:5])[C:7]=3[OH:28])[S:18][N:19]=2)=[CH:26][CH:25]=1

Participants

4

Reactant 3

HCID 750GlycineHCID 10942334Sodium MethoxideHCID 136344026HCID 136344026, compound

Product 1

HCID 135870681HCID 135870681, compoundYield 86.7%

Procedure

A mixture of 3-(4-Chloro-phenyl)-4-hydroxy-7-trimethylsilanylethynyl-isothiazolo[5,4-c]pyridine-5-carboxylic acid ethyl ester (51.5 mg, 0.119 mmol), glycine (269.7 mg, 3.59 mmol) and NaOMe (5.98 mL, 2.99 mmol, 0.5 M solution in MeOH) was refluxed for 24 h before it was concentrated in vacuo. The residue was dissolved in water (50 mL). The solution was then washed with CH2Cl2 (2×20 mL) before it was acidified by addition on aqueous 1N HCl solution. The resulting precipitate was sucked off, washed with water, and dried in vacuo to give the title compound (40 mg) as white solid: MS (m/z) 388.0 (M+1).

Workup

  1. temperaturewas refluxed for 24 h before it
  2. concentrationwas concentrated in vacuo
  3. dissolutionThe residue was dissolved in water (50 mL)
  4. washThe solution was then washed with CH2Cl2 (2×20 mL) before it
  5. additionwas acidified by addition on aqueous 1N HCl solution
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-c1c37223922e4d849a51bdf61f67af51
Source dataset
uspto-grants-2016_07
Patent number
US09387200B2

Reaction notes

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