Methanol → HCID 15557343, compound

HRID 267775Notes

Reaction equation

HRID 267775 reaction equation
C([O:4][C:5]1([CH2:21][N:22]([CH:26]([CH3:28])[CH3:27])C(=O)C)[CH2:11][O:10][C:9]2[CH:12]=[CH:13][C:14]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:15][C:8]=2[O:7][CH2:6]1)(=O)C.CO.[OH-].[Na+]>O>[OH:4][C:5]1([CH2:21][NH:22][CH:26]([CH3:28])[CH3:27])[CH2:11][O:10][C:9]2[CH:12]=[CH:13][C:14]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:15][C:8]=2[O:7][CH2:6]1

Participants

5

Reactant 3

HCID 887Methanol2×HCID 14798Sodium HydroxideHCID 54200507HCID 54200507, compound

Product 1

HCID 15557343HCID 15557343, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Acetoxy-3-(N-acetylisopropylaminomethyl)-7-methanesulfonamido-3,4-dihydro-2H-1,5-benzodioxepin (4.2 g., 10 millimole) in 20 ml. methanol is treated with 2 g. (50 millimoles) of sodium hydroxide in 20 ml. of methanol. The mixture is refluxed for 3 hours, cooled, and diluted with 400 mls. of water, neutralized with acid and extracted with ether. The combined ethereal solutions are washed with water, dried over anhydrous sodium sulfate, and evaporated to give 3-hydroxy-3-isopropylaminomethyl-7-methanesulfonamido-3,4-dihydro-2H-1,5-benzodioxepin.

Workup

  1. temperatureThe mixture is refluxed for 3 hours
  2. temperaturecooled
  3. additiondiluted with 400 mls
  4. extractionextracted with ether
  5. washThe combined ethereal solutions are washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-56f0c84f35e14713973e39e6bb314ea6
Source dataset
uspto-grants-1976_03
Patent number
US03944560

Reaction notes

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