Ethyl Acetate → HCID 68312658, compound

HRID 1530689Notes

Reaction equation

HRID 1530689 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10](=O)[C:11]([O:23][C:24]1[CH:46]=[CH:45][C:27]2[C:28]3[N:32]([CH2:33][CH2:34][O:35][C:26]=2[CH:25]=1)[CH:31]=[C:30]([C:36]1[N:37]([CH:42]([CH3:44])[CH3:43])[N:38]=[C:39]([CH3:41])[N:40]=1)[N:29]=3)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:12](OCC)=[O:13])C.CCOC(C)=O.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1>[CH:42]([N:37]1[C:36]([C:30]2[N:29]=[C:28]3[N:32]([CH2:33][CH2:34][O:35][C:26]4[CH:25]=[C:24]([O:23][C:11]([C:17]5[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=5)([CH2:12][OH:13])[CH2:10][OH:9])[CH:46]=[CH:45][C:27]=43)[CH:31]=2)=[N:40][C:39]([CH3:41])=[N:38]1)([CH3:44])[CH3:43]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 9357Potassium Sodium TartrateHCID 21226445Aluminium lithium hydrideHCID 68312845HCID 68312845, compound

Product 1

HCID 68312658HCID 68312658, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LiAlH4 (15 mg, 0.389 mmol) in THF (2 mL) was added a solution of 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]-2-phenylmalonic acid diethyl ester (72.5 mg, 0.13 mmol) in THF (1 mL). The mixture was stirred at RT for 2 h, then EtOAc (5 mL) was added and stirring was continued for 10 min. An aqueous solution of Rochelle's salt was then added and stirring continued for a further 30 min. 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 4-12% MeOH in DCM) affording the title compound (28.1 mg, 46%). LCMS (Method B): RT 2.75 min [M+H]+ 476

Workup

  1. stirringstirring
  2. waitwas continued for 10 min
  3. stirringstirring
  4. waitcontinued for a further 30 min
  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 4-12% MeOH in DCM)

Sources & evidence

ORD record
ord-95563d459abf45ec86272062fc0fe9d2
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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