Water → HCID 131715123, compound

HRID 977973Notes

Reaction equation

HRID 977973 reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:12]([O:14][C:15](=[O:34])[CH2:16][C:17](=[O:33])[N:18]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=1)[CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH3:13].C(=O)([O-])[O-].[K+].[K+].O>C1C=CC=CC=1>[CH2:12]([O:14][C:15](=[O:34])[CH2:16][C:17](=[O:33])[N:18]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])=[CH:28][CH:27]=1)[CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 131715122HCID 131715122, compound

Product 1

HCID 131715123HCID 131715123, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of benzyloxycarbonyl chloride (539 mg) in benzene (1.5 ml) is added dropwise to a mixture of ethyl[N-(p-aminobenzyl)-N-(methoxycarbonylethyl)carbamoyl]acetate (810 mg), potassium carbonate (595 mg), benzene (10 ml) and water (10 ml) at a temperature of 8° C. under stirring. The mixture is stirred at the same temperature for 30 minutes. The mixture is extracted with ethyl acetate, and the extract is washed with water, dried and then distilled to remove the solvent. The residue is purified by silica gel column chromatography (solvent, ethyl acetate:benzene=3:7) to give ethyl[N-(p-(N-benzyloxycarbonylamino)benzyl)-N-(methoxycarbonylethyl)carbamoyl]acetate (1.08 g, 94.2%) as colorless oil.

Workup

  1. stirringThe mixture is stirred at the same temperature for 30 minutes
  2. extractionThe mixture is extracted with ethyl acetate
  3. washthe extract is washed with water
  4. customdried
  5. distillationdistilled
  6. customto remove the solvent
  7. customThe residue is purified by silica gel column chromatography (solvent, ethyl acetate:benzene=3:7)

Sources & evidence

ORD record
ord-daad50426aa24b089999f363a20bb792
Source dataset
uspto-grants-1987_05
Patent number
US04663319

Reaction notes

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