Methanol → HCID 15675400, compound

HRID 1461272Notes

Reaction equation

HRID 1461272 reaction equation
[N:1]1([CH2:7][C:8]2[O:12][C:11]([CH2:13][NH:14][CH2:15][CH2:16][N:17]3[CH2:21][CH2:20][NH:19][C:18]3=[C:22]([C:25]#[N:26])[C:23]#[N:24])=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:27](OC(=O)C)(=[O:29])[CH3:28].CO>N1C=CC=CC=1>[C:27]([N:14]([CH2:15][CH2:16][N:17]1[CH2:21][CH2:20][NH:19][C:18]1=[C:22]([C:23]#[N:24])[C:25]#[N:26])[CH2:13][C:11]1[O:12][C:8]([CH2:7][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:9][CH:10]=1)(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 131846HCID 131846, compound

Product 1

HCID 15675400HCID 15675400, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 12 ml of pyridine was dissolved 0.6 g (1.69 mmol) of Compound 28, and 260 mg (2.55 mmol) of acetic anhydride was added dropwise. The reaction mixture was stirred at room temperature for 0.5 hour and, after addition of 1 ml of methanol, the solvent was distilled off. The residue was diluted with 20 ml of water, adjusted to pH 13 with 5N sodium hydroxide solution and extracted with methylene chloride. The extract was washed with saturated aqueous sodium chloride solution twice and dried over anhydrous magnesium sulfate. Finally the solvent was distilled off to give 0.66 g (97.9%) of Compound 44 as colorless oil.

Workup

  1. additionwas added dropwise
  2. distillationthe solvent was distilled off
  3. additionThe residue was diluted with 20 ml of water
  4. extractionextracted with methylene chloride
  5. washThe extract was washed with saturated aqueous sodium chloride solution twice
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationFinally the solvent was distilled off

Sources & evidence

ORD record
ord-f841c88dc09642f9b9d1d43be21a53ed
Source dataset
uspto-grants-1991_12
Patent number
US05075301

Reaction notes

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