Ethyl Acetate → HCID 68313136, compound

HRID 1530444Notes

Reaction equation

HRID 1530444 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10](=O)[CH:11]([O:20][C:21]1[CH:43]=[CH:42][C:24]2[C:25]3[N:29]([CH2:30][CH2:31][O:32][C:23]=2[CH:22]=1)[CH:28]=[C:27]([C:33]1[N:34]([CH:39]([CH3:41])[CH3:40])[N:35]=[C:36]([CH3:38])[N:37]=1)[N:26]=3)[CH2:12][CH:13]([CH3:19])[C:14](OCC)=[O:15])C.CCOC(C)=O.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1>[CH:39]([N:34]1[C:33]([C:27]2[N:26]=[C:25]3[N:29]([CH2:30][CH2:31][O:32][C:23]4[CH:22]=[C:21]([O:20][CH:11]([CH2:12][CH:13]([CH3:19])[CH2:14][OH:15])[CH2:10][OH:9])[CH:43]=[CH:42][C:24]=43)[CH:28]=2)=[N:37][C:36]([CH3:38])=[N:35]1)([CH3:41])[CH3:40]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 9357Potassium Sodium TartrateHCID 21226445Aluminium lithium hydrideHCID 68313011HCID 68313011, compound

Product 1

HCID 68313136HCID 68313136, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LiAlH4 (85 mg, 2.23 mmol) in THF (1 mL) at 0° C. 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]-4-methylpentanedioic acid diethyl ester (391 mg, 0.744 mmol) in THF (20 mL) and stirring at RT was continued for 2.5 h. To the reaction mixture was added EtOAc (2 mL) and stirring was continued for 30 min. An aqueous solution (10%) of Rochelle's salt was then added and the mixture was stirred for 5 min. Organic solvents were removed under reduced pressure and the resulting aqueous phase was extracted with EtOAc (×2). The combined organic phases were washed with water, followed by brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 3-18% MeOH in DCM) affording 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]-4-methylpentane-1,5-diol as a colorless gum (181 mg, 55%). LCMS: RT 2.49 min [M+H]+ 442.3

Workup

  1. stirringstirring
  2. waitwas continued for 30 min
  3. stirringthe mixture was stirred for 5 min
  4. customOrganic solvents were removed under reduced pressure
  5. extractionthe resulting aqueous phase was extracted with EtOAc (×2)
  6. washThe combined organic phases were washed with water
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customThe resulting residue was purified by column chromatography (Si-PCC, gradient 3-18% MeOH in DCM)

Sources & evidence

ORD record
ord-c3af069f89194c288b84f93fab65bcc0
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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