Sodium Hydroxide → 1-[3-(4-Bromobenzoyl)propionyl]-L-proline

HRID 903444Notes

Reaction equation

HRID 903444 reaction equation
C[O:2][C:3](=[O:22])[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9](=[O:21])[CH2:10][CH2:11][C:12](=[O:20])[C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=1.[OH-].[Na+]>>[Br:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]([CH2:11][CH2:10][C:9]([N:5]2[CH2:6][CH2:7][CH2:8][C@H:4]2[C:3]([OH:22])=[O:2])=[O:21])=[O:20])=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 228124471-[3-(4-Bromobenzoyl)propionyl]-L-proline methyl ester

Product 1

HCID 543439991-[3-(4-Bromobenzoyl)propionyl]-L-proline

Procedure

A mixture of 2.64 g. of 1-[3-(4-bromobenzoyl)propionyl]-L-proline methyl ester (Example 26) and 26 ml. of 1 N sodium hydroxide is stirred at room temperature. The solids are collected by decantation, dissolved in tetrahydrofuran and returned to the alkaline solution which is stirred further at room temperature. This alkaline solution is washed with ethyl acetate and poured into iced hydrochloric acid. This mixture is extracted with dichloromethane. The organic extract is dried over magnesium sulfate and evacuated to dryness in vacuo leaving a gum. This gum is triturated with ether giving white crystals which are recrystallized from acetone-hexane giving the desired product as 1.35 g. of white crystals, mp. 138°-139° C.

Workup

  1. additionA mixture of 2.64 g
  2. customThe solids are collected by decantation
  3. dissolutiondissolved in tetrahydrofuran
  4. washThis alkaline solution is washed with ethyl acetate
  5. additionpoured into iced hydrochloric acid
  6. extractionThis mixture is extracted with dichloromethane
  7. extractionThe organic extract
  8. dry with materialis dried over magnesium sulfate
  9. customevacuated to dryness in vacuo
  10. customleaving a gum
  11. customThis gum is triturated with ether giving white crystals which
  12. customare recrystallized from acetone-hexane giving the desired product as 1.35 g

Sources & evidence

ORD record
ord-3b60a7f4d5dd4e778589b36f500403ac
Source dataset
uspto-grants-1980_10
Patent number
US04226775

Reaction notes

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