Dicyclohexano-18-crown-6 → HCID 57261350, compound

HRID 341968Notes

Reaction equation

HRID 341968 reaction equation
[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[C:13]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)=[C:12]([NH:23][S:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[N:11]=[C:10]([CH:37]=[O:38])[N:9]=1)(=[O:3])[CH3:2].C1CC2[O:45]CCOCCOC3C(OCCOCCOC2CC1)CCCC3.[Mn]([O-])(=O)(=O)=O.[K+]>C1C=CC=CC=1>[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[C:13]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)=[C:12]([NH:23][S:24]([C:27]2[CH:28]=[CH:29][C:30]([C:33]([CH3:34])([CH3:36])[CH3:35])=[CH:31][CH:32]=2)(=[O:25])=[O:26])[N:11]=[C:10]([C:37]([OH:45])=[O:38])[N:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 85955Dicyclohexano-18-crown-6HCID 516875Potassium PermanganateHCID 57295961HCID 57295961, compound

Product 1

HCID 57261350HCID 57261350, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

0.27 g of 2-[6-(4-tert.butyl-phenylsulphonylamino)-2-formyl-5-(3-methoxy-phenoxy)-pyrimidin-4-yloxy]-ethyl acetate and 0.19 g of dicyclohexyl-18-crown-6 in 15 ml of benzene were stirred with 0.078 g of potassium permanganate at 2000 for 16 hours. The reaction mixture was partitioned between toluene and water. The organic phase was dried and evaporated, and the residue was purified over silica gel with chloroform-methanol. 0.09 g of 4-(2-acetoxy-ethoxy)-6-(4-tert.butyl-phenylsulphonylamino)-5-(3-methoxy-phenoxy)-pyrimidine-2-carboxylic acid was obtained as a foam, MS: (M-H)- 558.

Workup

  1. customThe reaction mixture was partitioned between toluene and water
  2. customThe organic phase was dried
  3. customevaporated
  4. customthe residue was purified over silica gel with chloroform-methanol

Sources & evidence

ORD record
ord-75af54caab9b4a82a6a91bc5afaf2108
Source dataset
uspto-grants-1999_01
Patent number
US05856484

Reaction notes

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