Potassium Carbonate → HCID 68506916, compound

HRID 2069455Notes

Reaction equation

HRID 2069455 reaction equation
[CH2:1]([N:3]([CH2:26][CH3:27])[C:4]1[N:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:20]=[C:19]([CH3:21])[C:18]([OH:22])=[C:17]([CH2:23][CH3:24])[CH:16]=3)[N:11]=2)[CH:7]=[C:6]([CH3:25])[N:5]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].C[O:35][C:36](=O)[CH:37](Cl)[C:38](OC)=[O:39].[BH4-].[Na+]>C(#N)C.CCOC(C)=O.O>[CH2:26]([N:3]([CH2:1][CH3:2])[C:4]1[N:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:20]=[C:19]([CH3:21])[C:18]([O:22][CH:37]([CH2:38][OH:39])[CH2:36][OH:35])=[C:17]([CH2:23][CH3:24])[CH:16]=3)[N:11]=2)[CH:7]=[C:6]([CH3:25])[N:5]=1)[CH3:27]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 120070Dimethyl chloromalonateHCID 4311764Sodium borohydrideHCID 136339878HCID 136339878, compound

Product 1

HCID 68506916HCID 68506916, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of Intermediate 11 (150 mg, 0.41 mmol) in acetonitrile (10 mL) are added K2CO3 (80 mg, 0.61 mmol) and dimethylchloromalonate (82 mg, 0.49 mmol). The reaction mixture is stirred at 65° C. for 3 h, and is then diluted with EtOAc, washed with water, dried over MgSO4, filtered and evaporated. The residue is purified by prep. TLC (eluting with Heptane/EA 4:1) and is then dissolved in ethanol (10 mL). NaBH4 (60 mg, 1.59 mmol) is added and the reaction mixture is stirred at rt for 3 h. After cooling to 5° C., water is added and the compound is extracted twice with EtOAc. The org. phase is dried over MgSO4, filtered, concentrated and purified by prep. TLC (eluting with Heptane/EA 1:1) to give the title compound as a yellow wax (54 mg); LC-MS: tR=1.06 min; [M+H]+=442.0.

Workup

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue is purified by prep
  6. washTLC (eluting with Heptane/EA 4:1)
  7. dissolutionis then dissolved in ethanol (10 mL)
  8. stirringthe reaction mixture is stirred at rt for 3 h
  9. temperatureAfter cooling to 5° C.
  10. extractionthe compound is extracted twice with EtOAc
  11. dry with materialphase is dried over MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated
  14. custompurified by prep
  15. washTLC (eluting with Heptane/EA 1:1)

Sources & evidence

ORD record
ord-416f7df892074a16a40e7ae39a2c85b5
Source dataset
uspto-grants-2012_10
Patent number
US08299086B2

Reaction notes

Loading…