Triethylamine → HCID 67396082, compound

HRID 714639Notes

Reaction equation

HRID 714639 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[S:12][C:11]([C:13](O)=[O:14])=[CH:10][CH:9]=1.C(N(CC)CC)C.ClC(OCC(C)C)=O.[BH4-].[Na+].C(=O)(O)[O-].[Na+]>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[S:12][C:11]([CH2:13][OH:14])=[CH:10][CH:9]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 16060158HCID 16060158, compound

Product 1

HCID 67396082HCID 67396082, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

350 mg (1.47 mmol) of the compound from Example 48A were dissolved in 5 ml of THF, the mixture was cooled to 0° C. and 0.20 ml (1.47 mmol) of triethylamine and 0.21 ml (1.61 mmol) of isobutyl chloroformate were added. The mixture was stirred at 0° C. for 1 h. The suspension was then filtered through a Seitz frit into a flask cooled to 0° C., and the residue was rinsed with about 2 ml of THF. With vigorous stirring, the filtrate obtained was then added to a solution, cooled to 0° C., of 166 mg (4.40 mmol) of sodium borohydride in 2 ml of water. After 1 h, 5 ml of saturated sodium bicarbonate solution were added and the mixture was warmed to RT. The mixture was extracted with 15 ml of ethyl acetate. The organic phase was washed successively with in each case 5 ml of saturated sodium bicarbonate solution and saturated sodium chloride solution. After drying over sodium sulfate, the mixture was filtered and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1, then 5:1). This gave 252 mg (63% of theory) of the title compound in a purity of 83%.

Workup

  1. filtrationThe suspension was then filtered through a Seitz frit into a flask
  2. temperaturecooled to 0° C.
  3. washthe residue was rinsed with about 2 ml of THF
  4. customWith vigorous stirring, the filtrate obtained
  5. additionwas then added to a solution
  6. waitAfter 1 h
  7. temperaturethe mixture was warmed to RT
  8. extractionThe mixture was extracted with 15 ml of ethyl acetate
  9. washThe organic phase was washed successively with in each case 5 ml of saturated sodium bicarbonate solution and saturated sodium chloride solution
  10. dry with materialAfter drying over sodium sulfate
  11. filtrationthe mixture was filtered
  12. concentrationconcentrated under reduced pressure
  13. customThe crude product was purified by chromatography on silica gel (mobile phase

Sources & evidence

ORD record
ord-af3ee4515efd4693a91403fc5d63bc18
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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