Heptane → HCID 18188678, compound

HRID 2269795Notes

Reaction equation

HRID 2269795 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:30]=[CH:29][C:15]2[C:16]3[C:24]([O:25][CH:26]([F:28])[F:27])=[CH:23][CH:22]=[CH:21][C:17]=3[O:18][C:19](=[O:20])[C:14]=2[C:13]=1[Br:31])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].CCCCCCC.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>ClCCl.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:30]=[CH:29][C:15]2[C:16]3[C:24]([O:25][CH:26]([F:28])[F:27])=[CH:23][CH:22]=[CH:21][C:17]=3[O:18][CH:19]([OH:20])[C:14]=2[C:13]=1[Br:31])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8900HeptaneHCID 166653HydrideHCID 9855836Potassium sodium tartarateHCID 18188911HCID 18188911, compound

Product 1

HCID 18188678HCID 18188678, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of Example 27D (0.52 g, 1.08 mmol) in dichloromethane (100 mL) at −78° C. was treated with disobutylaluminum hydride in heptane (1.30 mL, 1.30 mmol), stirred for 30 minutes at −78° C., and treated with ethyl acetate (10 mL) and sodium potassium tartrate (50 mL) to provide two layers. The layers were separated, and the aqueous layer was extracted with ethyl acetate. The extract was dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 20-50% ethyl acetate/hexanes to provide the desired product. MS (ESI(−)Q1MS) m/z 490 (M−H)−.

Workup

  1. customto provide two layers
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe extract was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash column chromatography on silica gel with 20-50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-8ffa268e127642c6bd957d43e1f4fb2e
Source dataset
uspto-grants-2001_12
Patent number
US06329534B1

Reaction notes

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