Methanol → HCID 54520100, compound

HRID 1605187Notes

Reaction equation

HRID 1605187 reaction equation
C[O:2][C:3](=[O:23])[C@H:4]([CH2:15][C:16]1(C)[CH:21]=[CH:20][CH:19]=[CH:18][CH2:17]1)[NH:5][C:6]([O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7].[CH3:24]O.[OH-].[Na+].S(=O)(=O)(O)O>O>[CH3:24][C:9]1([O:8][C:6]([NH:5][C@H:4]([C:3]([OH:2])=[O:23])[CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:7])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 68137264HCID 68137264, compound

Product 1

HCID 54520100HCID 54520100, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

Saponification of the above ester is accomplished by dissolving the oil in 10 ml. of methanol; 10 ml. of water is added and the pH of the mixture adjusted to 12 by addition of 1 N sodium hydroxide. The reaction is allowed to stir for 46 hours at 25°C. The pH of the reaction is adjusted to 7 by addition of 2 N sulfuric acid. The methanol solvent is removed in vacuo, saturated sodium bicarbonate is added to the residual aqueous solution, and then washed twice with ether. The reaction mixture is acidified by dropwise addition of concentrated sulfuric acid to pH 3.0, extracted three times with ethyl acetate, wash the combined organic layers twice with sodium chloride solution and dry over sodium sulfate. After removing the solvent in vacuo, 758 mg. of substantially pure N-(1-methylcyclohexyloxycarbonyl)-phenylalanine is obtained.

Workup

  1. dissolutionby dissolving the oil in 10 ml
  2. customThe methanol solvent is removed in vacuo, saturated sodium bicarbonate
  3. additionis added to the residual aqueous solution
  4. washwashed twice with ether
  5. additionThe reaction mixture is acidified by dropwise addition of concentrated sulfuric acid to pH 3.0
  6. extractionextracted three times with ethyl acetate
  7. washwash the combined organic layers twice with sodium chloride solution
  8. dry with materialdry over sodium sulfate
  9. customAfter removing the solvent in vacuo, 758 mg

Sources & evidence

ORD record
ord-adfc13e463984df086cbc90bce749fbe
Source dataset
uspto-grants-1976_04
Patent number
US03948971

Reaction notes

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