Sodium Hydroxide → HCID 117729163, compound

HRID 2200058Notes

Reaction equation

HRID 2200058 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH2:13])[N:8]([CH2:10][CH2:11][CH3:12])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl[C:17]([O:19][CH2:20][C:21]([Cl:24])([Cl:23])[Cl:22])=[O:18]>C(OCC)(=O)C.O>[Cl:22][C:21]([Cl:24])([Cl:23])[CH2:20][O:19][C:17](=[O:18])[NH:13][C:7]1[N:8]([CH2:10][CH2:11][CH3:12])[N:9]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 870632,2,2-Trichloroethyl chloroformateHCID 46196678HCID 46196678, compound

Product 1

HCID 117729163HCID 117729163, compoundYield 103.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred mixture of Intermediate 23a (0.774 g, 4.27 mmol) in ethyl acetate (4 mL) and 1 M aqueous NaOH (7.7 mL, 7.7 mmol) was added 2,2,2-trichloroethyl chloroformate (0.62 mL, 4.50 mmol) and the mixture was stirred at room temperature for 1.5 h. The mixture was diluted with water (50 mL) and extracted with ethyl acetate (2×25 mL). The combined organic extracts were washed with water and saturated aqueous NaCl, then evaporated to give the title compound (1.57 g) as an oil. LCMS (Method 3): Rt 4.28 min, m/z 356/358/360 [MH+]. 1H NMR (300 MHz, CDCl3): 0.90 (3H, t, J 7.5 Hz), 1.28 (9H, s), 1.78-1.87 (2H, m), 3.92 (2H, t, J 7.4 Hz), 4.83 (2H, s), 6.08 (1H, s), 6.46 (1H, s).

Workup

  1. extractionextracted with ethyl acetate (2×25 mL)
  2. washThe combined organic extracts were washed with water and saturated aqueous NaCl
  3. customevaporated

Sources & evidence

ORD record
ord-2082db6aaf744f2eb7d630b96669144d
Source dataset
uspto-grants-2016_06
Patent number
US09359354B2

Reaction notes

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