Hydrochloric Acid → HCID 66797546, compound

HRID 1045386Notes

Reaction equation

HRID 1045386 reaction equation
Br[C:2]1[CH:21]=[CH:20][C:5]2[O:6][CH2:7][CH2:8][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[S:10](=[O:12])(=[O:11])[C:4]=2[CH:3]=1.[B:22](OC(C)C)([O:27]C(C)C)[O:23]C(C)C.[Li]CCCC.Cl>C1COCC1>[C:16]([O:15][C:13]([N:9]1[CH2:8][CH2:7][O:6][C:5]2[CH:20]=[CH:21][C:2]([B:22]([OH:27])[OH:23])=[CH:3][C:4]=2[S:10]1(=[O:12])=[O:11])=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 66797550HCID 66797550, compoundHCID 178418339Butyllithium

Product 1

HCID 66797546HCID 66797546, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-65 °C

Procedure

To a solution of the product obtained in Step F above (21.6 g, 57.3 mmol) and 40 ml of triisopropyl borate in 210 ml of THF, cooled to −65° C. and under N2, there are added dropwise 90 ml (143 mmol) of 1.6M nBuLi solution. The reaction mixture is stirred for 1 hour at −65° C. and allowed to return to ambient temperature. After stirring for 1 hour, the solution is cooled in an ice bath and hydrolysed by adding 320 ml of 0.5M HCl solution. After extracting 3 times with CH2Cl2, the organic phase is washed with brine, dried over MgSO4 and evaporated. The residue is taken up in heptane and, after evaporation, is triturated in heptane and filtered to yield the title product.

Workup

  1. customto return to ambient temperature
  2. stirringAfter stirring for 1 hour
  3. temperaturethe solution is cooled in an ice bath
  4. extractionAfter extracting 3 times with CH2Cl2
  5. washthe organic phase is washed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customafter evaporation
  9. customis triturated in heptane
  10. filtrationfiltered

Sources & evidence

ORD record
ord-3c47c2512ca2400c8f65ab06c2115896
Source dataset
uspto-grants-2013_10
Patent number
US08569285B2

Reaction notes

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