4-Phenylsemicarbazide → HCID 70359839, compound

HRID 1651671Notes

Reaction equation

HRID 1651671 reaction equation
[CH:1]([C@H:3]1[C@@H:8]([CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:7][O:6][C@@H:5]([CH3:19])[O:4]1)=O.[C:20]1([NH:26][C:27](=[O:30])[NH:28][NH2:29])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)(=O)C.CO.C(Cl)(Cl)Cl>[CH3:18][O:17][C:15]([CH2:14][CH2:13][CH2:12]/[CH:11]=[CH:10]\[CH2:9][C@H:8]1[CH2:7][O:6][C@@H:5]([CH3:19])[O:4][C@H:3]1[CH:1]=[N:29][NH:28][C:27]([NH:26][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:30])=[O:16]

Participants

6

Reactant 2

HCID 108374-PhenylsemicarbazideHCID 14621471HCID 14621471, compound

Product 1

HCID 70359839HCID 70359839, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

A mixture of (2R,4R,5S)-4-formyl-5-[(Z)-6-methoxycarbonyl-2-hexenyl]-2-methyl-1,3-dioxane (300 mg), 4-phenylsemicarbazide (227 mg) and a few drops of acetic acid in methanol (5 ml) was stirred at room temperature for 3 hours and the mixture was diluted with chloroform (30 ml). The solution was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was chromatographed on a silica gel column (15 g) with a mixture of n-hexane and ethyl acetate (3:1) as an eluent to give (2R,4R,5S)-5-[(Z)-6-methoxycarbonyl-2-hexenyl]-2-methyl-4-(4-phenylsemicarbazonomethyl)-1,3-dioxane (403 mg) as an pale yellow oil.

Workup

  1. washThe solution was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was chromatographed on a silica gel column (15 g) with a mixture of n-hexane and ethyl acetate (3:1) as an eluent

Sources & evidence

ORD record
ord-d9cc3dd5da1c4d59beeffd5e4dec0b4c
Source dataset
uspto-grants-1990_05
Patent number
US04929639

Reaction notes

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