Citric Acid → HCID 54294658, compound

HRID 542648Notes

Reaction equation

HRID 542648 reaction equation
[CH3:1]I.[H-].[Na+].[CH2:5](OC(N[C@@H](C(O)=O)C)=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl.[C:22](=[O:25])([OH:24])[O-].[Na+].C(O)(=O)C[C:29]([CH2:34][C:35]([OH:37])=[O:36])(C(O)=O)O.[CH3:40][N:41](C)C=O>O1CCCC1.CCOCC.O>[CH3:1][O:37][C:35](=[O:36])[C@@H:34]([CH3:29])[N:41]([C:22]([O:24][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:25])[CH3:40]

Participants

11

Reactant 7

HCID 311Citric AcidHCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 70832N-Cbz-d-alanineHCID 516892Sodium Bicarbonate

Product 1

HCID 54294658HCID 54294658, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl iodide (25 ml.), then sodium hydride (50% in oil, 7.2 g.), were added with stirring to a solution of N-benzyloxycarbonyl-D-alanine (11.16 g.) in tetrahydrofuran (125 ml.) and dimethylformamide (13 ml.). The mixture was then stirred under reflux for 24 hours. Water (100 ml.) was added, the pH was adjusted to 5.5 with hydrochloric acid and sodium bicarbonate, and the solvents were stripped. The residue was distributed between ether and aqueous citric acid (5%). The ether layer was washed successively with water, saturated aqueous sodium bicarbonate, water and saturated aqueous sodium chloride, then dried over sodium sulfate and stripped of ehter, affording N-benzyloxycarbonyl-N-methyl-D-alanine methyl ester as a red oil (14.5 g.), which still contained the oil from the sodium hydride-oil mixture. TLC (silica gel, 3:1 hexane-ethyl acetate) of the red oil showed a single spot (Rf ~0.5).

Workup

  1. temperatureunder reflux for 24 hours
  2. washThe ether layer was washed successively with water, saturated aqueous sodium bicarbonate, water and saturated aqueous sodium chloride
  3. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-b11133682a1e4e1694cf58577060f829
Source dataset
uspto-grants-1987_04
Patent number
US04658013

Reaction notes

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