Water → HCID 9904109, compound

HRID 427473Notes

Reaction equation

HRID 427473 reaction equation
[CH3:1]C(C)([O-])C.[Na+].IC.[O:9]=[C:10]1[NH:15][C:14]2[CH:16]=[C:17]([C:19]3[C:20](=[O:29])[NH:21][C:22]4[C:27]([CH:28]=3)=[CH:26][CH:25]=[CH:24][CH:23]=4)[NH:18][C:13]=2[CH:12]=[CH:11]1.O>C1COCC1>[CH3:1][N:15]1[C:10](=[O:9])[CH:11]=[CH:12][C:13]2[NH:18][C:17]([C:19]3[C:20](=[O:29])[NH:21][C:22]4[C:27]([CH:28]=3)=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:16][C:14]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 9900259HCID 9900259, compoundHCID 23676156Sodium t-butoxide2×

Product 1

HCID 9904109HCID 9904109, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium tert-butoxide (10 mg, 0.11 mmol, 1.0 equiv) and iodomethane (13 μL, 0.22 mmol, 2.0 equiv) were added sequentially to a suspension of the product from Example 3 (30 mg, 0.11 mmol, 1 equiv) in THF (10 mL) at 23° C. The reaction mixture was stirred for 20 hours. Additional sodium tert-butoxide (20 mg, 0.22 mmol, 2.0 equiv) and iodomethane (26 μL, 0.44 mmol, 4.0 equiv) were added in 2 equal portions over 1 hour, and then the reaction mixture was allowed to stir an additional 1 hour. Water (5 mL) was added, and the resulting mixture was concentrated to a volume of 2 mL. The mixture was purified by reverse phase HPLC to afford the titled compound as a yellow solid.

Workup

  1. stirringto stir an additional 1 hour
  2. concentrationthe resulting mixture was concentrated to a volume of 2 mL
  3. customThe mixture was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-0680d389db804a07988a6919fc32fa68
Source dataset
uspto-grants-2001_11
Patent number
US06313138B1

Reaction notes

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