Trimethylaluminum → HCID 59527659, compound

HRID 1808921Notes

Reaction equation

HRID 1808921 reaction equation
[CH2:1]([N:8]([C:15]([C:17]1([CH2:20][NH:21][C:22]([O:24]C(C)(C)C)=O)[CH2:19][CH2:18]1)=[O:16])[C@H:9](C(OC)=O)[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Al](C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O.C1(C)C=CC=CC=1>[CH2:1]([N:8]1[C@@H:9]([CH3:10])[C:22](=[O:24])[NH:21][CH2:20][C:17]2([CH2:19][CH2:18]2)[C:15]1=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 16682925Trimethylaluminum2×HCID 59527666HCID 59527666, compound

Product 1

HCID 59527659HCID 59527659, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2.8 g (7.2 mmol) 2-1 in 75 mL CH2Cl2 and 5 mL TFA was allowed to stir at room temperature overnight. The solvents were removed by rotary evaporation, the residue was basified with saturated aqueous Na2CO3, and extracted with three portions of 2:1 CHCl3/EtOH. The organic extracts were concentrated, redissolved in CH2Cl2, filtered and concentrated to provide a brown oil. This material was dissolved in 75 mL of toluene, cooled to 0° C. and 8.4 mL (16.9 mmol) of a 2 M solution of AlMe3 in toluene was added dropwise. The reaction was allowed to slowly warm to room temperature overnight with stirring. An additional 2 mL of AlMe3 was added and stirring was continued for an additional 24 h. The reaction was cooled to 0° C., carefully quenched with 100 mL of 1M HCl, and extracted with 3 portions of EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4 and concentrated to provide 2-2 as a white taffy. Data for 2-2: LC/MS: rt=1.38 min; m/z (M+H)=258.1. found; 258.1 required.

Workup

  1. customThe solvents were removed by rotary evaporation
  2. extractionextracted with three portions of 2:1 CHCl3/EtOH
  3. concentrationThe organic extracts were concentrated
  4. dissolutionredissolved in CH2Cl2
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto provide a brown oil
  8. temperaturecooled to 0° C.
  9. temperatureto slowly warm to room temperature overnight
  10. stirringwith stirring
  11. stirringstirring
  12. waitwas continued for an additional 24 h
  13. temperatureThe reaction was cooled to 0° C.
  14. customcarefully quenched with 100 mL of 1M HCl
  15. extractionextracted with 3 portions of EtOAc
  16. washThe combined organic extracts were washed with brine
  17. dry with materialdried over Na2SO4
  18. concentrationconcentrated
  19. customto provide 2-2 as a white taffy
  20. customrt=1.38 min

Sources & evidence

ORD record
ord-d80d8ac785a941a5945e9bf40a116ec3
Source dataset
uspto-grants-2013_01
Patent number
US08362009B2

Reaction notes

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