Propylene Oxide → HCID 21391891, compound

HRID 461687Notes

Reaction equation

HRID 461687 reaction equation
O1C(C)C1.[H-].[Na+].[CH2:7]1[O:9][CH:8]1[CH2:10][OH:11].C(S([C:17]1[S:18][C:19]([C:22]([NH:24][CH2:25][CH2:26][C:27]23[CH2:36][CH:31]4[CH2:32][CH:33]([CH2:35][CH:29]([CH2:30]4)[CH2:28]2)[CH2:34]3)=[O:23])=[CH:20][N:21]=1)(=O)=O)C>O1CCCC1>[O:9]1[CH:8]([CH2:10][O:11][C:17]2[S:18][C:19]([C:22]([NH:24][CH2:25][CH2:26][C:27]34[CH2:36][CH:31]5[CH2:32][CH:33]([CH2:35][CH:29]([CH2:30]5)[CH2:28]3)[CH2:34]4)=[O:23])=[CH:20][N:21]=2)[CH2:7]1

Participants

6

Reactant 4

HCID 6378Propylene OxideHCID 11164GlycidolHCID 24758Sodium hydrideHCID 21391889HCID 21391889, compound

Product 1

HCID 21391891HCID 21391891, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-5 °C

Procedure

This example illustrates further processes of the invention for preparing the 1,2-epoxypropane compounds of formula B. In this example 0.0525 mole of sodium hydride in a 50% mineral oil mixture is stirred in 300 ml. of anhydrous tetrahydrofuran, under nitrogen, then cooled to -30° C and 0.055 mole of glycidol is added dropwise. The mixture is allowed to warm to -5° C and stirred for 10 minutes and then recooled to -30° C. A solution of 0.05 mole of 2-ethylsulfonyl-5-[2-(adamant-1-yl)ethylaminocarbonyl]thiazole in 100 ml. of anhydrous tetrahydrofuran is added dropwise and the resulting mixture allowed to warm to 0° C. Additional solvent is added as needed to facilitate stirring. The mixture is maintained at 30 minutes at 0° C and then poured into 500 ml. of ethyl acetate, extracted with 100 ml. of water, and then with 100 ml. of aqueous saturated sodium chloride and dried over anhydrous magnesium sulfate and filtered. The filtrate is evaporated under dryness affording oily residue which is then further purified by chromatography on silica gel eluting with 40% ethyl acetate- 60% hexane, by vol., affording 1,2-epoxy-3-[5-(2-[adamant-1-yl]ethylaminocarbonyl)thiazol-2-yloxy]propane.

Workup

  1. customrecooled to -30° C
  2. temperatureto warm to 0° C
  3. additionAdditional solvent is added
  4. stirringto facilitate stirring
  5. temperatureThe mixture is maintained at 30 minutes at 0° C
  6. additionpoured into 500 ml
  7. extractionof ethyl acetate, extracted with 100 ml
  8. dry with materialof aqueous saturated sodium chloride and dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customThe filtrate is evaporated under dryness
  11. customaffording oily residue which
  12. customis then further purified by chromatography on silica gel eluting with 40% ethyl acetate- 60% hexane, by vol.

Sources & evidence

ORD record
ord-875d21d3638e4eaea0a36d70384df09c
Source dataset
uspto-grants-1977_12
Patent number
US04064135

Reaction notes

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