Water → HCID 19853911, compound

HRID 1722656Notes

Reaction equation

HRID 1722656 reaction equation
[H-].[Na+].C[C:4](OS(C1C=CC(C)=CC=1)(=O)=O)([CH2:21][CH2:22][CH3:23])[CH2:5][C:6]1[C:15]([NH:16][C:17](=[O:19])[CH3:18])=[CH:14][CH:13]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[C:7]=1[OH:20].O.[CH2:36]1COCC1>C(OCC)(=O)C>[CH3:36][C:22]1([CH3:23])[CH2:21][CH2:4][CH2:5][C:6]2[C:15]([NH:16][C:17](=[O:19])[CH3:18])=[CH:14][CH:13]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[C:7]=2[O:20]1

Participants

6

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 19853883HCID 19853883, compound

Product 1

HCID 19853911HCID 19853911, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2.2 g sodium hydride (60%) and 20 ml THF is added dropwise at 0° C. a solution of 15 g of methyl 3-(2'-methyl-2'-tosyloxypentyl)-4-acetylaminosalicylate in 10 ml THF. This is allowed to come to room temperature over several hours, then chilled and 2 ml H2O added slowly. This is then diluted with ethyl acetate, the salts filtered off, washed with water and brine, dried and concentrated to dryness to obtain methyl 2,2-dimethyl-6-acetylamino-2,3,4,5-tetrahydro-1-benzoxepin-9-carboxylate which is used directly in the next step.

Workup

  1. waitto come to room temperature over several hours
  2. temperaturechilled
  3. filtrationthe salts filtered off
  4. washwashed with water and brine
  5. customdried
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-e697175c2ee64a1fbf325998940ac486
Source dataset
uspto-grants-1989_08
Patent number
US04857517

Reaction notes

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