Methyl tyrosinate hydrochloride → Folic acid tyrosine methyl ester

HRID 1156490Notes

Reaction equation

HRID 1156490 reaction equation
[C:1]([O-:32])(=[O:31])[CH2:2][CH2:3][C@H:4]([NH:8][C:9]([C:11]1[CH:30]=[CH:29][C:14]([NH:15][CH2:16][C:17]2[N:28]=[C:27]3[C:20]([N:21]=[C:22]([NH:24][C:25]3=[O:26])[NH2:23])=[N:19][CH:18]=2)=[CH:13][CH:12]=1)=[O:10])[C:5]([OH:7])=[O:6].[Na+].Cl.C(N=C=NCCCN(C)C)C.Cl.[CH3:47][O:48][C:49](=[O:60])[C@H:50]([CH2:52][C:53]1[CH:58]=[CH:57][C:56]([OH:59])=[CH:55][CH:54]=1)[NH2:51]>O>[CH3:47][O:48][C:49](=[O:60])[C@H:50]([CH2:52][C:53]1[CH:54]=[CH:55][C:56]([OH:59])=[CH:57][CH:58]=1)[NH2:51].[C:1]([OH:32])(=[O:31])[CH2:2][CH2:3][C@H:4]([NH:8][C:9]([C:11]1[CH:12]=[CH:13][C:14]([NH:15][CH2:16][C:17]2[N:28]=[C:27]3[C:20]([N:21]=[C:22]([NH:24][C:25]3=[O:26])[NH2:23])=[N:19][CH:18]=2)=[CH:29][CH:30]=1)=[O:10])[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 76956Methyl tyrosinate hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 136359212Sodium folate

Product 1

HCID 136359211Folic acid tyrosine methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Sodium folate (100 mg.) is dissolved in water (10 ml.). To this is added 1-ethyl-3-(3 dimethylaminopropyl)carbodiimide hydrochloride (100 mg.), followed by the addition of tyrosine methyl ester hydrochloride (32 mg.) dissolved in water (2 ml.). A yellow gelatinous precipitate forms. The mixture is stirred for four hours at room temperature. The precipitated material is extracted into ethyl acetate and washed successively with 1 N sodium bicarbonate (3×10 ml.) 1 N hydrochloric acid (3×10 ml.) and water (2×10 ml.). The solution is dried over anhydrous magnesium sulfate and the ethyl acetate removed on a rotary evaporator. Trituration of the remaining residues with hexane yields yellow crystalline folic acid tyrosine methyl ester conjugate weighing 56 mg.

Workup

  1. extractionThe precipitated material is extracted into ethyl acetate
  2. washwashed successively with 1 N sodium bicarbonate (3×10 ml.) 1 N hydrochloric acid (3×10 ml.) and water (2×10 ml.)
  3. dry with materialThe solution is dried over anhydrous magnesium sulfate
  4. customthe ethyl acetate removed on a rotary evaporator

Sources & evidence

ORD record
ord-6df24563178a4476a4b6787d8b578541
Source dataset
uspto-grants-1982_06
Patent number
US04336185

Reaction notes

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