Sodium Hydroxide → HCID 117728992, compound

HRID 2200023Notes

Reaction equation

HRID 2200023 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[N:9][N:10]([CH2:12][CH2:13][OH:14])[CH:11]=2)[N:5]=[C:4]([CH:15]([CH3:17])[CH3:16])[CH:3]=1.[OH-].[Na+].Cl[C:21]([O:23][CH2:24][C:25]([Cl:28])([Cl:27])[Cl:26])=[O:22]>CCOC(C)=O>[Cl:26][C:25]([Cl:28])([Cl:27])[CH2:24][O:23][C:21](=[O:22])[NH:1][C:2]1[N:6]([C:7]2[CH:8]=[N:9][N:10]([CH2:12][CH2:13][OH:14])[CH:11]=2)[N:5]=[C:4]([CH:15]([CH3:17])[CH3:16])[CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 870632,2,2-Trichloroethyl chloroformateHCID 117729041HCID 117729041, compound

Product 1

HCID 117728992HCID 117728992, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of Intermediate Ab (250 mg, 1.06 mmol) in EtOAc (3 mL) was treated with aqueous NaOH (1M, 1.9 mmol), followed by 2,2,2-trichloroethyl chloroformate (154 μL, 1.16 mmol) and the reaction mixture was stirred at RT for 1 h. The mixture was partitioned between EtOAc (10 mL) and water (10 mL). The layers were separated and the aqueous layer was extracted with a further 10 mL EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by FCC, using 0-40% EtOAc in DCM to afford the title compound as a colorless oil (300 mg, 70%). LCMS (Method 3): Rt 3.42 min, m/z 410, 412 [MH+].

Workup

  1. customThe mixture was partitioned between EtOAc (10 mL) and water (10 mL)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with a further 10 mL EtOAc
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-38fd3f4167724a35b6ae39634776b454
Source dataset
uspto-grants-2016_06
Patent number
US09359354B2

Reaction notes

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