Methane → HCID 19363189, compound

HRID 850337Notes

Reaction equation

HRID 850337 reaction equation
[CH:1]1([CH2:7][NH:8][CH:9]([C:13]2[CH:18]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:16]([OH:23])=[C:15]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:14]=2)[C:10](O)=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:28]([NH2:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.ON1C2C=CC=CC=2N=N1.C>CO.C(Cl)Cl>[CH2:28]([NH:35][C:10](=[O:11])[CH:9]([NH:8][CH2:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[C:13]1[CH:18]=[C:17]([C:19]([CH3:21])([CH3:20])[CH3:22])[C:16]([OH:23])=[C:15]([C:24]([CH3:25])([CH3:27])[CH3:26])[CH:14]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 297MethaneHCID 7504BenzylamineHCID 757711-HydroxybenzotriazoleHCID 19363152HCID 19363152, compound

Product 1

HCID 19363189HCID 19363189, compoundYield 22.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a methylene chloride (5 mL) solution of Example 22 (0.36 g, 0.96 mmol) was added benzyl amine (110 mg, 1.0 mmol), N,N1 -dicyclohexylcarbodiimide (DCC) (206 mg, 1.0 mmol), and 1-hydroxybenzotriazole (HOBT) (135 mg, 1.0 mmol). The solution was stirred at room temperature for 24 hours. The mixture was filtered free of insolubles and the filtrate evaporated to give an oil. The oil was dissolved in methanol (30 mL) treated with charcoal and evaporated to a foam. The foam was dissolved in ethyl acetate (75 mL) and washed with saturated sodium bicarbonate (50 mL) and then dried over magnesium sulfate. This was purified by chromatography (125 g silica gel, 2% methanol in methylene chloride). The appropriate fractions were combined and evaporated in vacuo to give 0.10 g (22%) of product.

Workup

  1. filtrationThe mixture was filtered free of insolubles
  2. customthe filtrate evaporated
  3. customto give an oil
  4. customevaporated to a foam
  5. dissolutionThe foam was dissolved in ethyl acetate (75 mL)
  6. washwashed with saturated sodium bicarbonate (50 mL)
  7. dry with materialdried over magnesium sulfate
  8. customThis was purified by chromatography (125 g silica gel, 2% methanol in methylene chloride)
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-d85a6a0da3dd499b805413f9c50a8471
Source dataset
uspto-grants-2000_01
Patent number
US06017918

Reaction notes

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