Formamide → HCID 10075893, compound

HRID 1613512Notes

Reaction equation

HRID 1613512 reaction equation
[CH:1]([NH2:3])=O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:5].Br[CH2:19][C:20]([C:22]1[CH:49]=[CH:48][C:25]([O:26][CH2:27][CH2:28][CH2:29][O:30][C:31]2[CH:44]=[CH:43][C:34]3[CH2:35][CH2:36][CH:37]([C:39]([O:41][CH3:42])=[O:40])[O:38][C:33]=3[C:32]=2[CH2:45][CH2:46][CH3:47])=[C:24]([CH2:50][CH:51]=[CH2:52])[C:23]=1[O:53][CH3:54])=O.C(=O)([O-])[O-].[Mg+2]>O1CCOCC1.C(OCC)C>[CH3:54][O:53][C:23]1[C:24]([CH2:50][CH:51]=[CH2:52])=[C:25]([CH:48]=[CH:49][C:22]=1[C:20]1[N:3]=[CH:1][S:5][CH:19]=1)[O:26][CH2:27][CH2:28][CH2:29][O:30][C:31]1[CH:44]=[CH:43][C:34]2[CH2:35][CH2:36][CH:37]([C:39]([O:41][CH3:42])=[O:40])[O:38][C:33]=2[C:32]=1[CH2:45][CH2:46][CH3:47]

Participants

7

Reactant 4

HCID 713FormamideHCID 11029Magnesium CarbonateHCID 14817Phosphorus sulfide (P2S5)HCID 10008314HCID 10008314, compound

Product 1

HCID 10075893HCID 10075893, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent2×

Procedure

Formamide (0.15 mL, 4.3 mmol) and phosphorus pentasulfide (0.33 g, 0.73 mmol) in 15 mL dioxane were refluxed for 2 hr., and 4 mL of this solution was added to 59 mg of the compound of Example 15 in 2 mL dioxane with 100 mg magnesium carbonate. The reaction mixture was refluxed for 1.75 hr. and poured into ethyl ether/1N sodium hydroxide. The ether layer was washed with brine, dried over sodium sulfate, and concentrated. Flash chromatography on silica gel using 8:1 hexane/ethyl acetate as eluant gave the product (28 mg, 52 μmmol, 51% yield). High resolution mass spectrum, m/e 537.2195 (calculated for C30H35NO6S, 537.2185).

Workup

  1. temperatureThe reaction mixture was refluxed for 1.75 hr
  2. washThe ether layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customFlash chromatography on silica gel using 8:1 hexane/ethyl acetate as eluant gave the product (28 mg, 52 μmmol, 51% yield)

Sources & evidence

ORD record
ord-7d7c85c50aa84e2ca890a01c10d6d965
Source dataset
uspto-grants-1993_03
Patent number
US05192782

Reaction notes

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