HCID 19036658, compound → HCID 86750581, compound

HRID 976333Notes

Reaction equation

HRID 976333 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]>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

3

Reactant 1

HCID 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 0.1 M 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 ag. 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. additionpoured
  2. additioninto dilute ag
  3. extractionHCl, extracted with EtOAc
  4. washwashed with sat'd NaHCO3
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-be2185021f72408b995e6e06a0f5f5d8
Source dataset
uspto-grants-1997_03
Patent number
US05612355

Reaction notes

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