Sulfuric Acid → HCID 42613157, compound

HRID 2387830Notes

Reaction equation

HRID 2387830 reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[N:12]=[C:11]([NH:13][C@@H:14]([CH2:17][CH2:18][CH3:19])[CH2:15][OH:16])[C:10]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][C:28]([OH:30])=[O:29])=[CH:23][C:22]=2[O:31][CH3:32])=[C:9]([CH3:33])[N:8]=1.[C:34]([O-])(O)=O.[Na+]>CO>[NH2:6][C:7]1[N:12]=[C:11]([NH:13][C@@H:14]([CH2:17][CH2:18][CH3:19])[CH2:15][OH:16])[C:10]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][C:28]([O:30][CH3:34])=[O:29])=[CH:23][C:22]=2[O:31][CH3:32])=[C:9]([CH3:33])[N:8]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 68953524(S)-2-(4-((2-Amino-4-(1-hydroxypentan-2-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxyphenyl)acetic acid

Product 1

HCID 42613157HCID 42613157, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

Concentrated sulfuric acid (0.3 mL) was added to a solution of the product from step (v) (0.09 g) in MeOH (1 mL). The solution was heated at 70° C. for 3 h and then poured into saturated aqueous NaHCO3 solution (10 mL). The aqueous was extracted with EtOAC and the combined organic phases were dried, filtered and evaporated. The crude product was purified by RPHPLC to give the title compound, 0.007 g.

Workup

  1. extractionThe aqueous was extracted with EtOAC
  2. customthe combined organic phases were dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was purified by RPHPLC

Sources & evidence

ORD record
ord-4bcd1082768f483e975b5ce5d1fc9927
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

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