Sodium Hydroxide → Z-Trp-Ser-OH

HRID 1415336Notes

Reaction equation

HRID 1415336 reaction equation
[NH:1]([C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])[C@H:2]([C:13]([NH:15][C@H:16]([C:19]([O:21]C)=[O:20])[CH2:17][OH:18])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.CC1C(C2(C3C(C)=CC(O)=C(C(C)C)C=3)OC(=O)C3C2=CC=CC=3)=CC(C(C)C)=C(O)C=1.[OH-].[Na+]>O1CCOCC1.O>[NH:1]([C:23]([O:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:24])[C@H:2]([C:13]([NH:15][C@H:16]([C:19]([OH:21])=[O:20])[CH2:17][OH:18])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 31316ThymolphthaleinHCID 12821032Carbobenzyloxytryptophylserine methyl ester

Product 1

HCID 14827444Z-Trp-Ser-OH

Reagents, catalysts & solvents 1

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

Procedure

4.4 g (10 mmols) of Z-Trp-Ser-OMe were dissolved in 30 ml of dioxane/water (4:1) and mixed with a spatula tip of thymolphthaleine. The mixture was titrated, while stirring, with 1N NaOH until a constant blue color was obtained. 10 ml were consumed. 10 ml of 1N hydrochloric acid were added and the reaction mixture was evaporated. The residue was distributed between ethyl acetate and water. The ethyl acetate phase was dried with Na2SO4 and concentrated. The residue was triturated with petroleum ether. Yield: 3.2 g (75%). It was recrystallized from ethyl acetate/petroleum ether. Yield: 3 g (70%), melting point: 148° C.

Workup

  1. customwas obtained
  2. custom10 ml were consumed
  3. addition10 ml of 1N hydrochloric acid were added
  4. customthe reaction mixture was evaporated
  5. dry with materialThe ethyl acetate phase was dried with Na2SO4
  6. concentrationconcentrated
  7. customThe residue was triturated with petroleum ether
  8. customIt was recrystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-c9d43e571c424009b45dee94c696d2c3
Source dataset
uspto-grants-1977_01
Patent number
US04003884

Reaction notes

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