HCID 13532751, compound → HCID 13532783, compound

HRID 1906265Notes

Reaction equation

HRID 1906265 reaction equation
[OH:1][CH2:2][N:3]1[C:8](=[O:9])[CH2:7][N:6]([CH2:10][CH2:11][N:12]2[CH2:17][C:16](=[O:18])[N:15]([CH2:19][OH:20])[C:14](=[O:21])[CH2:13]2)[CH2:5][C:4]1=[O:22].C(OC([NH:33][C:34]1[CH:42]=[CH:41][C:37]([C:38](Cl)=[O:39])=[CH:36][CH:35]=1)=O)C1C=CC=CC=1>N1C=CC=CC=1>[NH2:33][C:34]1[CH:42]=[CH:41][C:37]([C:38]([O:20][CH2:19][N:15]2[C:14](=[O:21])[CH2:13][N:12]([CH2:11][CH2:10][N:6]3[CH2:7][C:8](=[O:9])[N:3]([CH2:2][O:1][C:38](=[O:39])[C:37]4[CH:36]=[CH:35][C:34]([NH2:33])=[CH:42][CH:41]=4)[C:4](=[O:22])[CH2:5]3)[CH2:17][C:16]2=[O:18])=[O:39])=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 13532751HCID 13532751, compoundHCID 14394264Benzyl [4-(chlorocarbonyl)phenyl]carbamate

Product 1

HCID 13532783HCID 13532783, compoundYield 114.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of 1,2-bis(4-hydroxymethyl-3,5-dioxopiperazin-1-yl)ethane (0.63 g, 2.0 m mol) and pyridine (10 ml), p-benzyloxycarbonylaminobenzoyl chloride (1.27 g, 4.4 m mol) dissolved in pyridine (12 ml) was added gradually at 0° C. and then the reaction mixture was stirred for 1 hour at 0° C. and successively for 16 hours at room temperature. The residue obtained by removing the solvent from the reaction mixture under reduced pressure was added to water (50 ml) and extracted with chloroform (150 ml×2). The extract solution was washed with 10% sulfuric acid solution and successively with water, further was washed with saturated sodium bicarbonate aqueous solution and successively with water and was dried. The residue obtained by removing the solvent from the extract solution was purified by silica gel column chromatography (ethyl acetate) to give benzyloxycarbonyl derivative of the titled compound (1.27 g; yield 77.4%). The derivative (1.27 g) was dissolved in a mixture of ethyl acetate (80 ml) and ethanol (80 ml), and 10% palladium-carbon (0.13 g) was added and the mixture was stirred overnight under hydrogen at room temperature. The reaction mixture was filtered and the filtrate was concentrated. The residue obtained was purified by silica gel column chromatography (chloroform:methanol=95:5) and recrystallized from ether to give the titled compound (0.39 g; yield 45.7%).

Workup

  1. additionwas added gradually at 0° C.
  2. customThe residue obtained
  3. customby removing the solvent from the reaction mixture under reduced pressure
  4. additionwas added to water (50 ml)
  5. extractionextracted with chloroform (150 ml×2)
  6. washThe extract solution was washed with 10% sulfuric acid solution and successively with water
  7. washfurther was washed with saturated sodium bicarbonate aqueous solution and successively with water
  8. customwas dried
  9. customThe residue obtained
  10. customby removing the solvent from the extract solution
  11. customwas purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-bcad88d9bd31422f8bfc0d6cdd226385
Source dataset
uspto-grants-1987_03
Patent number
US04650799

Reaction notes

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