Potassium Hydroxide → HCID 178437558, compound

HRID 1729501Notes

Reaction equation

HRID 1729501 reaction equation
[OH-].[K+].[Br:3][C:4]1[C:8]2[CH:9]=[C:10]([CH2:13][N:14]3[C:18]([C:19]([O:21]CC)=[O:20])=[C:17]([CH:24]4[CH2:26][CH2:25]4)[N:16]=[C:15]3[CH2:27][CH3:28])[CH:11]=[CH:12][C:7]=2[O:6][C:5]=1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[C:35]1[NH:39][N:38]=[N:37][N:36]=1>O.C(O)C>[Br:3][C:4]1[C:8]2[CH:9]=[C:10]([CH2:13][N:14]3[C:18]([C:19]([OH:21])=[O:20])=[C:17]([CH:24]4[CH2:26][CH2:25]4)[N:16]=[C:15]3[CH2:27][CH3:28])[CH:11]=[CH:12][C:7]=2[O:6][C:5]=1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[C:35]1[NH:39][N:38]=[N:37][N:36]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 178468477HCID 178468477, compound

Product 1

HCID 178437558HCID 178437558, compoundYield 61.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Potassium hydroxide (1.2 g) in water (5 ml) was added to a suspension of the product of Example 1 (0.5 g) in ethanol (15 ml) and the mixture stirred at 55° for 18 h. The solvent was evaporated and the residue partitioned between water (25 ml) and ether (3×25 ml). The aqueous phase was acidified to pH1 with hydrochloric acid (2N, 15 ml) and extracted with ethyl acetate (3×30 ml). The combined ethyl acetate extracts were washed with brine (50 ml) and dried. The solvent was concentrated in vacuo resulting in the precipitation of a colourless solid which was filtered off and washed with ether (2×5 ml) to give the title compound as a colourless solid (290 mg) m.p. 198°.

Workup

  1. customThe solvent was evaporated
  2. customthe residue partitioned between water (25 ml) and ether (3×25 ml)
  3. extractionextracted with ethyl acetate (3×30 ml)
  4. washThe combined ethyl acetate extracts were washed with brine (50 ml)
  5. customdried
  6. concentrationThe solvent was concentrated in vacuo
  7. customresulting in the precipitation of a colourless solid which
  8. filtrationwas filtered off
  9. washwashed with ether (2×5 ml)

Sources & evidence

ORD record
ord-4a374e04f5c24ca295b2e8f3821e8117
Source dataset
uspto-grants-1994_07
Patent number
US05332831

Reaction notes

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