Sodium Hydroxide → (S)-3-(4-Hydroxy-phenyl)-2-[2-((S)-2-mercapto-3-methyl-butyrylamino)-2-methyl-propionylamino]-propionic acid

HRID 1720862Notes

Reaction equation

HRID 1720862 reaction equation
C([O:3][C:4](=[O:31])[C@H:5]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)[NH:6][C:7](=[O:22])[C:8]([NH:11][C:12](=[O:21])[C@@H:13]([S:17]C(=O)C)[CH:14]([CH3:16])[CH3:15])([CH3:10])[CH3:9])C.[OH-].[Na+]>CO>[SH:17][C@@H:13]([CH:14]([CH3:16])[CH3:15])[C:12]([NH:11][C:8]([CH3:9])([CH3:10])[C:7]([NH:6][C@H:5]([C:4]([OH:31])=[O:3])[CH2:23][C:24]1[CH:25]=[CH:26][C:27]([OH:30])=[CH:28][CH:29]=1)=[O:22])=[O:21]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11797917HCID 11797917, compound

Product 1

HCID 9800134(S)-3-(4-Hydroxy-phenyl)-2-[2-((S)-2-mercapto-3-methyl-butyrylamino)-2-methyl-propionylamino]-propionic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-[2-(2(S)-acetylthio-3-methyl-1-oxobutylamino)-2-methyl-1-oxopropyl]-L-tyrosine ethyl ester (0.18 g, 0.39 mmol) in methanol (10 mL) is added 1N sodium hydroxide (1.55 mL, 1.55 mmol). The mixture is stirred for 5 hours and then the solvent is removed in vacuo. The residue is dissolved in water (50 mL) and washed with ethyl acetate (10 mL). The aqueous phase is acidified to pH 1 with 1N hydrochloric acid and extracted with ethyl acetate (3×50 mL). The organic phase is washed with brine, dried over magnesium sulfate and the solvent is concentrated to yield a clear oil which is crystallized from ethyl ether to give N-[2-(2(S)-mercapto-3-methyl-1-oxobutylamino)-2-methyl-1-oxopropyl]-L-tyrosine, m.p. 180°-181° C., the compound of formula II wherein R1 is 4-hydroxyphenyl, R2 and R3 are hydrogen, R4 is isopropyl, and R6 and R7 are methyl.

Workup

  1. customthe solvent is removed in vacuo
  2. dissolutionThe residue is dissolved in water (50 mL)
  3. washwashed with ethyl acetate (10 mL)
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. washThe organic phase is washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationthe solvent is concentrated
  8. customto yield a clear oil which
  9. customis crystallized from ethyl ether

Sources & evidence

ORD record
ord-74a03f25382243cd9b2ff9cf2064b9e2
Source dataset
uspto-grants-1996_04
Patent number
US05508266

Reaction notes

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