Sodium Hydroxide → HCID 53644777, compound

HRID 342473Notes

Reaction equation

HRID 342473 reaction equation
C([O:4][CH2:5][C:6]([NH:8][C:9]1[C:10]([Cl:32])=[C:11]([C:28]([Cl:31])=[CH:29][CH:30]=1)[C:12]([NH:14][C:15]1[C:23]2[O:22][C:21]3[CH2:24][CH2:25][CH2:26][CH2:27][C:20]=3[C:19]=2[CH:18]=[CH:17][CH:16]=1)=[O:13])=[O:7])(=O)C.[OH-].[Na+]>ClCCl.CO>[Cl:32][C:10]1[C:9]([NH:8][C:6](=[O:7])[CH2:5][OH:4])=[CH:30][CH:29]=[C:28]([Cl:31])[C:11]=1[C:12]([NH:14][C:15]1[C:23]2[O:22][C:21]3[CH2:24][CH2:25][CH2:26][CH2:27][C:20]=3[C:19]=2[CH:18]=[CH:17][CH:16]=1)=[O:13]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53705007HCID 53705007, compound

Product 1

HCID 53644777HCID 53644777, compoundYield 49.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-(3-acetoxyacetylamino-2,6-dichlorobenzoylamino)-1,2,3,4-tetrahydrodibenzofuran (67 mg) and aqueous 1N-sodium hydroxide (0.5 ml) in a mixture of dichloromethane (1 ml) and methanol (1 ml) was stirred at ambient temperature for 1 hour. The mixture was partitioned between a mixture of dichloromethane and ethanol (8:2) and water. The organic layer was separated, washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was crystallized from ethanol to give 6-(2,6-dichloro-3-hydroxyacetylamino-benzoylamino)-1,2,3,4-tetrahydrodibenzofuran (30 mg).

Workup

  1. customThe mixture was partitioned between a mixture of dichloromethane and ethanol (8:2) and water
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-3b0f7fb7e0da401f8abac7dc690b6b4a
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

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