HCID 14996941, compound → HCID 14996995, compound

HRID 1769714Notes

Reaction equation

HRID 1769714 reaction equation
[OH:1][CH:2]([C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:36])[NH:12][CH2:13][C:14]([N:16]([CH2:23][C:24](=[O:35])[N:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:28][CH2:27][CH2:26]2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:15])[CH:7]=[CH:8][CH:9]=1)[CH3:3]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[C:2]([C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:36])[NH:12][CH2:13][C:14]([N:16]([CH2:23][C:24](=[O:35])[N:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:28][CH2:27][CH2:26]2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:15])[CH:7]=[CH:8][CH:9]=1)(=[O:1])[CH3:3]

Participants

4

Reactant 1

HCID 14996941HCID 14996941, compound

Product 1

HCID 14996995HCID 14996995, compoundYield 37.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

2.3 g of manganese dioxide are added in 2 portions at a 20-hour interval to a solution of 0.8 g of (RS)-2-{3-[3-(1-hydroxyethyl)phenyl]ureido}-N-[2-oxo-2-(1,2,3,4-tetrahydro-1-quinolyl)ethyl]-N-phenylacetamide in 50 cm3 of methylene chloride. The mixture is stirred at a temperature close to 25° C for 70 hours. The insoluble product is separated off by filtration and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization from diisopropyl ether, 0.3 g of 2-[3-(3-acetylphenyl)ureido]-N-[2-oxo-2-(1,2,3,4-tetrahydro-1-quinolyl)ethyl]-N-phenylacetamide melting at 130° C is obtained.

Workup

  1. customclose to 25° C for 70 hours
  2. customThe insoluble product is separated off by filtration
  3. concentrationthe filtrate is concentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  4. customAfter recrystallization from diisopropyl ether

Sources & evidence

ORD record
ord-7fbf2d66073448ef9168f8ccf8d9b761
Source dataset
uspto-grants-1995_01
Patent number
US05382590

Reaction notes

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