Hydrochloric Acid → HCID 20204037, compound

HRID 977974Notes

Reaction equation

HRID 977974 reaction equation
[CH2:1]([O:3][C:4](=[O:33])[CH2:5][C:6](=[O:32])[N:7]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])=[CH:17][CH:16]=1)[CH2:8][CH2:9][C:10]([O:12]C)=O)[CH3:2].[O-]CC.[Na+].O.Cl>C1C=CC=CC=1>[CH2:25]([O:24][C:22]([NH:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:7]2[CH2:8][CH2:9][C:10](=[O:12])[CH:5]([C:4]([O:3][CH2:1][CH3:2])=[O:33])[C:6]2=[O:32])=[CH:16][CH:17]=1)=[O:23])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2723922Sodium ethoxideHCID 131715123HCID 131715123, compound

Product 1

HCID 20204037HCID 20204037, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of ethyl[N-(p-(N-benzyloxycarbonylamino)benzyl)-N-(methoxycarbonylethyl)carbamoyl]acetate (967 mg) in benzene (15 ml) is added dropwise to a solution of sodium ethoxide (prepared from sodium (60 mg) and ethanol (2 ml)) at room temperature. The mixture is stirred at the same temperature for 30 minutes. The mixture is poured into water. The aqueous solution is neutralized with 10% HCl, and extracted with ethyl acetate. The extract is washed with a saturated sodium chloride solution, dried and then distilled to remove the solvent to give ethyl 1-(p-(N-benzyloxycarbonylamino)-benzyl)-2,4-dioxopiperidine-3-carboxylate (841 mg, 93.5%) as colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract is washed with a saturated sodium chloride solution
  3. customdried
  4. distillationdistilled
  5. customto remove the solvent

Sources & evidence

ORD record
ord-1eb40a17c0d94a548c5d119a1448cd8a
Source dataset
uspto-grants-1987_05
Patent number
US04663319

Reaction notes

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