Sulfuric Acid → HCID 42613157, compound

HRID 1617176Notes

Reaction equation

HRID 1617176 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-c434d1e1f9ed4fa2807f9c7b7ecdfcc6
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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