Sodium Hydroxide → HCID 22865145, compound

HRID 343054Notes

Reaction equation

HRID 343054 reaction equation
C([S:4][C@@H:5]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:6]([NH:8][CH:9]1[CH2:19][CH2:18][CH2:17][C:12]2([CH2:16][CH2:15][CH2:14][CH2:13]2)[N:11]([CH2:20][C:21]([O:23]CC)=[O:22])[C:10]1=[O:26])=[O:7])(=O)C.[OH-].[Na+]>CO>[SH:4][C@@H:5]([CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:6]([NH:8][CH:9]1[CH2:19][CH2:18][CH2:17][C:12]2([CH2:16][CH2:15][CH2:14][CH2:13]2)[N:11]([CH2:20][C:21]([OH:23])=[O:22])[C:10]1=[O:26])=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86753585HCID 86753585, compound

Product 1

HCID 22865145HCID 22865145, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of the product from part (1) (232 mg., 0.43 mmol.) in methanol (5 ml., deoxygenated via nitrogen bubbling) was cooled to 0° C. and treated with 1N sodium hydroxide (5 ml., deoxygenated via nitrogen bubbling). After stirring for one hour at 0° C. while purging continuously with nitrogen, the reaction was warmed to room temperature. After a total of three hours, the reaction was acidified to pH 1 with 5% potassium bisulfate and extracted with ethyl acetate. The organic layers were combined, washed with water (50 ml.), brine, dried (sodium sulfate), filtered, concentrated in vacuo, and reevaporated from hexanes to give 204 mg. of title product as a white foam. HPLC indicates the product to be a 47:53 mixture of diastereomers. TLC (2:3 ethyl acetate:hexanes) Rf =0.22.

Workup

  1. customwhile purging continuously with nitrogen
  2. temperaturethe reaction was warmed to room temperature
  3. customAfter a total of three hours
  4. extractionextracted with ethyl acetate
  5. washwashed with water (50 ml.), brine
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customreevaporated from hexanes
  10. customto give 204 mg

Sources & evidence

ORD record
ord-f9f65810aaec4d589320b085aa4221e1
Source dataset
uspto-grants-1999_01
Patent number
US05859239

Reaction notes

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