Hydrochloric Acid → Boc-D-phe-pro-OH

HRID 2302212Notes

Reaction equation

HRID 2302212 reaction equation
[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@@H:2]([C:10]([N:12]1[CH2:20][CH2:19][CH2:18][C@H:13]1[C:14]([O:16]C)=[O:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+].Cl>O1CCOCC1.O>[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@@H:2]([C:10]([N:12]1[CH2:20][CH2:19][CH2:18][C@H:13]1[C:14]([OH:16])=[O:15])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11567002HCID 11567002, compound

Product 1

HCID 1797945Boc-D-phe-pro-OHYield 86.3%

Reagents, catalysts & solvents 1

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

Procedure

Boc-D-Phe-Pro-OMe (8.3 g) was dissolved in dioxane/water=6/4 v/v (150 ml) and treated with 2M sodium hydroxide solution (16.5 ml) portionwise over 1 h at room temperature, keeping the pH at 12.5. 2M hydrogen chloride solution was added to the reaction mixture until pH 3.0 and the water layer was extracted with ethyl acetate. The combined organic phases were washed with water, brine and dried over sodium sulfate, filtered and concentrated in vacuo to yield Boc-D-Phe-Pro-OH (6.9 g).

Workup

  1. extractionthe water layer was extracted with ethyl acetate
  2. washThe combined organic phases were washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b176a2d9bc9a4f2b9fd238e2e741a707
Source dataset
uspto-grants-2002_08
Patent number
US06432921B1

Reaction notes

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