HCID 59567461, compound → HCID 59567460, compound

HRID 2098305Notes

Reaction equation

HRID 2098305 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C@:4]([N:15]1[C:20](=[O:21])[N:19]2[CH:22]=[N:23][C:24]([C:25](=[O:27])[NH2:26])=[C:18]2[N:17]=[N:16]1)([CH3:14])[CH2:5][O:6][Si](C(C)(C)C)(C)C>Cl>[CH3:1][O:2][C:3](=[O:28])[C@:4]([N:15]1[C:20](=[O:21])[N:19]2[CH:22]=[N:23][C:24]([C:25](=[O:27])[NH2:26])=[C:18]2[N:17]=[N:16]1)([CH3:14])[CH2:5][OH:6]

Participants

3

Reactant 1

HCID 59567461HCID 59567461, compound

Product 1

HCID 59567460HCID 59567460, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(8-carbamoyl-4-oxo-imidazo[5,1-d][1,2,3,5]tetrazin-3-yl)-2-methyl-propionic acid methyl ester (80 mg, 0.21 mmol) was diluted in 1 mL of 1.25 M ethanolic HCl solution. The reaction mixture was then stirred at room temperature for 45 minutes, whereupon the mixture concentrated in vacuo. The crude residue was diluted in Et2O which promoted the formation of a precipitate. The solid was removed by vacuum filtration, washed with Et2O (3×1 reaction volumes) and purified by flash chromatography (SiO2) using CH2Cl2: MeOH (9:1) as eluent to give the title compound (38 mg, 61%) as a white solid. 1H NMR (400 MHz, d6-DMSO) δ ppm: 8.94 (1H, s), 7.91 (1H, s), 7.76 (1H, s), 5.70 (1H, dd, J=8.0 Hz, 6.0 Hz), 5.10 (OH, s (br), 1H), 4.11 (2H, multiplet), 3.70 (3H, s).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe crude residue was diluted in Et2O which
  3. customThe solid was removed by vacuum filtration
  4. washwashed with Et2O (3×1 reaction volumes)
  5. custompurified by flash chromatography (SiO2)

Sources & evidence

ORD record
ord-7ad539ff7e3542acbf1f6008035816d5
Source dataset
uspto-grants-2013_05
Patent number
US08450479B2

Reaction notes

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