Water → HCID 131723954, compound

HRID 1356720Notes

Reaction equation

HRID 1356720 reaction equation
[NH:1]([C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])[C@H:2]([C:10]([N:12]([CH3:21])[C@H:13]([C:17]([O:19]C)=[O:18])[CH:14]([CH3:16])[CH3:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O>O1CCOCC1.[OH-].[Na+]>[NH:1]([C:22]([O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:23])[C@H:2]([C:10]([N:12]([CH3:21])[C@H:13]([C:17]([OH:19])=[O:18])[CH:14]([CH3:16])[CH3:15])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 962WaterHCID 131723955HCID 131723955, compound

Product 1

HCID 131723954HCID 131723954, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of Z-Phe-N-Me-Val-OMe (3.39 g) in dioxane (40 ml), 2N NaOH (4 ml) was added, followed by stirring for 2 hours at 50° C. The reaction mixture was mixed with water and washed with methylene chloride. The aqueous layer was adjusted to pH3 by the addition of 10% hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and evaporated under reduced pressure to remove the solvent; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: methylene chloride:methanol=95:5) to give the titled compound (3.03 g, 92%).

Workup

  1. washwashed with methylene chloride
  2. additionThe aqueous layer was adjusted to pH3 by the addition of 10% hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customto remove the solvent

Sources & evidence

ORD record
ord-ccc7178ddc8a4c6ca8b975c77a18315b
Source dataset
uspto-grants-2003_07
Patent number
US06586630B1

Reaction notes

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