Sodium Hydroxide → HCID 21078377, compound

HRID 1374898Notes

Reaction equation

HRID 1374898 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([O:11][CH:12]([CH2:23][CH3:24])[C:13]([NH:15][C:16]([CH3:22])([CH3:21])[C:17]#[C:18][CH2:19][CH3:20])=[O:14])[CH:8]=[N:9][CH:10]=1)=[O:4].[OH-].[Na+]>CC(O)C.O>[C:3]([C:5]1[CH:6]=[C:7]([O:11][CH:12]([CH2:23][CH3:24])[C:13]([NH:15][C:16]([CH3:22])([CH3:21])[C:17]#[C:18][CH2:19][CH3:20])=[O:14])[CH:8]=[N:9][CH:10]=1)([OH:4])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21078399HCID 21078399, compound

Product 1

HCID 21078377HCID 21078377, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

The product from Stage 2 (2.18 g) was dissolved in propan-2-ol (25 ml) and a solution of sodium hydroxide (0.28 g) in water (10 ml) was added at ambient temperature. The mixture was stirred for 1.5 hours, stored at ambient temperature for 18 hours and evaporated under reduced pressure to remove the propan-2-ol. The residual aqueous solution was diluted with water, washed with ethyl acetate and the aqueous phase was acidified with hydrochloric acid. The acidic aqueous phase was extracted with ethyl acetate (three times) and the extracts were combined, washed with water (twice), dried over magnesium sulphate and evaporated under reduced pressure to give a solid. The solid was washed with a small volume of diethyl ether then filtered from solution to give the required product as a colourless solid; 1.47 g; m.p. 162–164° C.

Workup

  1. waitstored at ambient temperature for 18 hours
  2. customevaporated under reduced pressure
  3. customto remove the propan-2-ol
  4. additionThe residual aqueous solution was diluted with water
  5. washwashed with ethyl acetate
  6. extractionThe acidic aqueous phase was extracted with ethyl acetate (three times)
  7. washwashed with water (twice),
  8. dry with materialdried over magnesium sulphate
  9. customevaporated under reduced pressure
  10. customto give a solid
  11. washThe solid was washed with a small volume of diethyl ether
  12. filtrationthen filtered from solution

Sources & evidence

ORD record
ord-1b81d84ed5ad49a5a33adb715a067ebd
Source dataset
uspto-grants-2007_01
Patent number
US07166621B2

Reaction notes

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