Ethyl Acetate → HCID 68313055, compound

HRID 1530695Notes

Reaction equation

HRID 1530695 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10](=O)[C:11]([CH2:41][CH:42]1[CH2:44][CH2:43]1)([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>[CH:42]1([CH2:41][C:11]([O:17][C:18]2[CH:40]=[CH:39][C:21]3[C:22]4[N:26]([CH2:27][CH2:28][O:29][C:20]=3[CH:19]=2)[CH:25]=[C:24]([C:30]2[N:31]([CH:36]([CH3:38])[CH3:37])[N:32]=[C:33]([CH3:35])[N:34]=2)[N:23]=4)([CH2:10][OH:9])[CH2:12][OH:13])[CH2:44][CH2:43]1

Participants

6

Reactant 4

HCID 8857Ethyl Acetate2×HCID 9357Potassium Sodium TartrateHCID 21226445Aluminium lithium hydrideHCID 68312871HCID 68312871, compound

Product 1

HCID 68313055HCID 68313055, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
10 °C

Procedure

To a suspension of LiAlH4 (65.5 mg, 1.724 mmol) in THF (7 mL) cooled to 10° C. was added a solution of 2-cyclopropylmethyl-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 (309 mg, 0.575 mmol) in THF (5 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 was then added and stirring continued for a further 1.5 h. EtOAc was added and 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 as a colourless foam (0.20 g, 77%). LCMS (Method B): RT 2.72 min [M+H]+ 454.

Workup

  1. stirringstirring
  2. waitwas continued for 10 min
  3. stirringstirring
  4. waitcontinued for a further 1.5 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 4-12% MeOH in DCM)

Sources & evidence

ORD record
ord-216f831af1424aa9b7d3200b04402e02
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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