Hydrochloric Acid → HCID 42613159, compound

HRID 2387832Notes

Reaction equation

HRID 2387832 reaction equation
Cl.[NH2:2][C:3]1[N:8]=[C:7]([NH:9][C@@H:10]([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:11][OH:12])[C:6]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][C:25]([OH:27])=[O:26])=[CH:20][C:19]=2[O:28][CH3:29])=[C:5]([CH3:30])[N:4]=1.[C:31]([O-])(O)=O.[Na+]>CO>[NH2:2][C:3]1[N:8]=[C:7]([NH:9][C@@H:10]([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:11][OH:12])[C:6]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][C:25]([O:27][CH3:31])=[O:26])=[CH:20][C:19]=2[O:28][CH3:29])=[C:5]([CH3:30])[N:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium Bicarbonate2×HCID 68955143HCID 68955143, compound

Product 1

HCID 42613159HCID 42613159, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

Concentrated hydrochloric acid (1 mL) was added to a stirred solution of the product from step (i) (0.1 g) in MeOH (2 mL) and the mixture was heated at 70° C. for 2 h. The mixture was allowed to cool and then poured into saturated aqueous NaHCO3 solution (5 mL). The mixture was adjusted to pH ˜7 by adding NaHCO3 and the aqueous was extracted with EtOAc. The combined organic phase was dried, filtered and evaporated. The crude product was purified by RPHPLC to give the title compound, 0.014 g.

Workup

  1. temperatureto cool
  2. extractionthe aqueous was extracted with EtOAc
  3. customThe combined organic phase was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by RPHPLC

Sources & evidence

ORD record
ord-4912caeadacc4cc4b962f551ab644709
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

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