Ethyl Acetate → HCID 68313016, compound

HRID 1530710Notes

Reaction equation

HRID 1530710 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10](=O)[C:11]([CH2:41][CH:42]([CH3:44])[CH3:43])([O:17][C:18]1[CH:40]=[CH:39][C:21]2[C:22]3[N:26]([CH2:27][CH2:28][O:29][C:20]=2[CH:19]=1)[CH:25]=[C:24]([C:30]1[N:31]([CH:36]([CH3:38])[CH3:37])[N:32]=[C:33]([CH3:35])[N:34]=1)[N:23]=3)[C:12](OCC)=[O:13])C.CCOC(C)=O.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1>[CH2:41]([C:11]([O:17][C:18]1[CH:40]=[CH:39][C:21]2[C:22]3[N:26]([CH2:27][CH2:28][O:29][C:20]=2[CH:19]=1)[CH:25]=[C:24]([C:30]1[N:31]([CH:36]([CH3:38])[CH3:37])[N:32]=[C:33]([CH3:35])[N:34]=1)[N:23]=3)([CH2:12][OH:13])[CH2:10][OH:9])[CH:42]([CH3:44])[CH3:43]

Participants

6

Reactant 4

HCID 8857Ethyl Acetate2×HCID 9357Potassium Sodium TartrateHCID 21226445Aluminium lithium hydrideHCID 68312811HCID 68312811, compound

Product 1

HCID 68313016HCID 68313016, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice-cooled suspension of LiAlH4 (41.3 mg, 1.09 mmol) in THF (3 mL) was added a solution of 2-isobutyl-2-[2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-yloxy]malonic acid diethyl ester (195 mg, 0.362 mmol) in THF (2 mL). The reaction mixture was stirred at RT for 1.5 h. To the reaction mixture was added EtOAc (1 mL) and stirring was continued for 10 min. An aqueous solution of Rochelle salt's and EtOAc were then added and stirring continued for a further 1 h. The mixture was filtered through a Celite® pad and the aqueous phase was extracted with EtOAc. The combined organic phases were washed with brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 4-14% MeOH in DCM) affording the title compound as a colourless gum (88.6 mg, 54%). LCMS (Method B): RT 2.87 min [M+H]+ 456.

Workup

  1. stirringstirring
  2. waitwas continued for 10 min
  3. stirringstirring
  4. waitcontinued for a further 1 h
  5. filtrationThe mixture was filtered through a Celite® pad
  6. extractionthe aqueous phase was extracted with EtOAc
  7. washThe combined organic phases were washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo
  10. customThe resulting residue was purified by column chromatography (Si-PCC, gradient 4-14% MeOH in DCM)

Sources & evidence

ORD record
ord-bf1b6c82d1ff46e8880ce8d5d6b77ab9
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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