Ethyl Acetate → HCID 68313002, compound

HRID 1530440Notes

Reaction equation

HRID 1530440 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:14][C:15](=O)[C:16]([O:28][C:29]1[CH:51]=[CH:50][C:32]2[C:33]3[N:37]([CH2:38][CH2:39][O:40][C:31]=2[CH:30]=1)[CH:36]=[C:35]([C:41]1[N:42]([CH:47]([CH3:49])[CH3:48])[N:43]=[C:44]([CH3:46])[N:45]=1)[N:34]=3)([CH3:27])[CH2:17][CH2:18][O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)C1C=CC=CC=1.CCOC(C)=O.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1>[CH2:20]([O:19][CH2:18][CH2:17][C:16]([O:28][C:29]1[CH:51]=[CH:50][C:32]2[C:33]3[N:37]([CH2:38][CH2:39][O:40][C:31]=2[CH:30]=1)[CH:36]=[C:35]([C:41]1[N:42]([CH:47]([CH3:49])[CH3:48])[N:43]=[C:44]([CH3:46])[N:45]=1)[N:34]=3)([CH3:27])[CH2:15][OH:14])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 9357Potassium Sodium TartrateHCID 21226445Aluminium lithium hydrideHCID 68312931HCID 68312931, compound

Product 1

HCID 68313002HCID 68313002, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LiAlH4 (4.4 mg, 0.116 mmol) in THF (1 mL) was added a solution of 4-benzyloxy-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-methylbutyric acid benzyl ester (36 mg, 0.058 mmol) in THF (2 mL) and stirring at RT was continued for 2.5 h. To the reaction mixture was added EtOAc (0.5 mL) and stirring was continued for 10 min. An aqueous solution of Rochelle's salt was then added and the 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 3-12% MeOH in DCM) affording 4-Benzyloxy-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-methylbutan-1-ol (29 mg, 98%). 1H NMR (CDCl3, 400 MHz): δ 8.41 (1H, d, J=8.83 Hz), 7.60 (1H, s), 7.39-7.27 (5H, m), 6.81 (1H, dd, J=8.83, 2.41 Hz), 6.69 (1H, d, J=2.37 Hz), 5.98-5.85 (1H, m), 4.60-4.50 (2H, m), 4.49-4.35 (4H, m), 3.83-3.69 (2H, m), 3.65-3.55 (2H, m), 3.24 (1H, s), 2.42 (3H, s), 2.20-2.12 (1H, m), 2.07-1.97 (1H, m), 1.57 (6H, d, J=6.75 Hz), 1.31 (3H, s)

Workup

  1. stirringstirring
  2. waitwas continued for 10 min
  3. extractionthe aqueous phase was extracted with EtOAc (×2)
  4. washThe combined organic phases were washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by column chromatography (Si-PCC, gradient 3-12% MeOH in DCM)

Sources & evidence

ORD record
ord-f06da8b3d6b645c381adec5b1136d71d
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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