Water → N-Ac-D-Phe-2-Nal-OH

HRID 1636229Notes

Reaction equation

HRID 1636229 reaction equation
[NH:1]([C:29]([CH3:31])=[O:30])[C@@H:2]([C:10]([NH:12][C@H:13]([C:25]([O:27]C)=[O:26])[CH2:14][C:15]1[CH:24]=[C:23]2[C:18]([CH:19]=[CH:20][CH:21]=[CH:22]2)=[CH:17][CH:16]=1)=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+].O>O1CCOCC1.O>[NH:1]([C:29]([CH3:31])=[O:30])[C@@H:2]([C:10]([NH:12][C@H:13]([C:25]([OH:27])=[O:26])[CH2:14][C:15]1[CH:24]=[C:23]2[C:18]([CH:19]=[CH:20][CH:21]=[CH:22]2)=[CH:17][CH:16]=1)=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 73937193N-Ac-D-Phe-2-Nal-OMe

Product 1

HCID 73916679N-Ac-D-Phe-2-Nal-OHYield 113.5%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A solution of N-Ac-D-Phe-2-Nal-OMe (1.55 g) in 20 ml of dioxane/water=9/1 (v/v) was treated with sufficient 6N sodium hydroxide to keep the pH at 12 for 1 hours at room temperature. After acidification, the mixture was poured into water and was extracted with dichloromethane. The organic layer was washed with water and was dried on sodium sulfate. The filtrate was evaporated and yielded 1.7 g crude N-Ac-D-Phe-2-Nal-OH.

Workup

  1. customfor 1 hours
  2. customat room temperature
  3. extractionwas extracted with dichloromethane
  4. washThe organic layer was washed with water
  5. customwas dried on sodium sulfate
  6. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-b46995fb7d15494782325407a5877dac
Source dataset
uspto-grants-2000_03
Patent number
US06034067

Reaction notes

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