Hydrochloric Acid → HCID 86750581, compound

HRID 264345Notes

Reaction equation

HRID 264345 reaction equation
Br[CH2:2][C:3](=[O:27])[O:4][CH:5]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=1)[CH2:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8].Cl>C1COCC1>[C:25]([C:22]1[CH:23]=[CH:24][C:19]([CH2:18][CH2:17][CH2:16][CH2:15][C@H:5]2[O:4][C:3](=[O:27])[CH2:2][C@@:7]([OH:8])([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH2:6]2)=[CH:20][CH:21]=1)#[N:26]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19036658HCID 19036658, compound

Product 1

HCID 86750581HCID 86750581, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of the product of step B (2.71 g, 6.35 mmol) in dry THF (50 mL) at -78° C. under an atmosphere of nitrogen was added a 0.1M solution of SmI2 (135 mL, 13.5 mmol) over 10 minutes. The blue solution was stirred at -78° C. for 1 hour, poured into dilute aq. HCl, extracted with EtOAc, washed with sat'd NaHCO3, dried (MgSO4), filtered, and the solvent evaporated under reduced pressure. Silica gel chromatography (35-50% EtOAc/hexane) afforded 1.90 g (86%) of title product.

Workup

  1. extractionextracted with EtOAc
  2. washwashed with sat'd NaHCO3
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-2e32a5c3ef2a44999431e1278f6658c5
Source dataset
uspto-grants-1997_07
Patent number
US05646183

Reaction notes

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