Sodium Hydroxide → HCID 70394741, compound

HRID 1722185Notes

Reaction equation

HRID 1722185 reaction equation
C[O:2][C:3](=[O:33])[C@:4]([CH2:22][C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1)([CH2:18][CH:19]([CH3:21])[CH3:20])[NH:5][C:6](=[O:17])[CH2:7][CH2:8][C:9]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)=[O:10].[OH-].[Na+]>CO>[C:23]1([CH2:22][C@@:4]([C:3]([OH:33])=[O:2])([CH2:18][CH:19]([CH3:21])[CH3:20])[NH:5][C:6](=[O:17])[CH2:7][CH2:8][C:9]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[O:10])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70395830HCID 70395830, compound

Product 1

HCID 70394741HCID 70394741, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 380 mg of the ester compound in 5 ml of methyl alcohol was added 0.92 ml of a 1Naqueous sodium hydroxide solution with stirring under ice-cooling, and the mixture was stirred overnight. The reaction mixture was evaporated under reduced pressure, and water was added to the residue. The mixture was washed with ethyl ether. The aqueous layer was adjusted to a pH of 2to 3 by adding a 1N hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure to obtain 288 mg of 2-(1-naphthylmethyl)-3-morpholinocarbonylpropionyl-L-leucine as a white powder.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred overnight
  3. customThe reaction mixture was evaporated under reduced pressure, and water
  4. additionwas added to the residue
  5. washThe mixture was washed with ethyl ether
  6. additionby adding a 1N hydrochloric acid
  7. extractionextracted with ethyl acetate
  8. washThe ethyl acetate layer was washed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9c961de5965f4ea1adffc75e9f45b302
Source dataset
uspto-grants-1989_08
Patent number
US04853463

Reaction notes

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