Glutaric anhydride → 5-(4-[(4aS,8aR)-4-(3,4-Diethoxy-phenyl)-1-oxo-4a,5,8,8a-tetrahydro-1H-phthalazin-2-yl]-piperidin-1-yl)-5-oxo-pentanoic Acid

HRID 491439Notes

Reaction equation

HRID 491439 reaction equation
[C:1]1(=[O:8])[O:7][C:5](=[O:6])[CH2:4][CH2:3][CH2:2]1.[CH2:9]([O:11][C:12]1[CH:13]=[C:14]([C:21]2[C@@H:30]3[C@@H:25]([CH2:26][CH:27]=[CH:28][CH2:29]3)[C:24](=[O:31])[N:23]([CH:32]3[CH2:37][CH2:36][N:35](S(C4C=CC(C)=CC=4)(=O)=O)[CH2:34][CH2:33]3)[N:22]=2)[CH:15]=[CH:16][C:17]=1[O:18][CH2:19][CH3:20])[CH3:10]>>[CH2:9]([O:11][C:12]1[CH:13]=[C:14]([C:21]2[C@@H:30]3[C@@H:25]([CH2:26][CH:27]=[CH:28][CH2:29]3)[C:24](=[O:31])[N:23]([CH:32]3[CH2:33][CH2:34][N:35]([C:5](=[O:6])[CH2:4][CH2:3][CH2:2][C:1]([OH:7])=[O:8])[CH2:36][CH2:37]3)[N:22]=2)[CH:15]=[CH:16][C:17]=1[O:18][CH2:19][CH3:20])[CH3:10]

Participants

3

Reactant 2

HCID 7940Glutaric anhydrideHCID 10175016(4aS,8aR)-4-(3,4-Diethoxyphenyl)-2-[1-(toluene-4-sulfonyl)-piperidin-4-yl]-4a,5,8,8a-tetrahydro-2H-phthalazin-1-one

Product 1

HCID 101960635-(4-[(4aS,8aR)-4-(3,4-Diethoxy-phenyl)-1-oxo-4a,5,8,8a-tetrahydro-1H-phthalazin-2-yl]-piperidin-1-yl)-5-oxo-pentanoic Acid

Procedure

Prepared from glutaric anhydride and starting compound A2 as described for compound 1. After evaporating the pyridine, the residue is partitioned between ethyl acetate and 1N hydrochloric acid. The ethyl acetate solution is dried over magnesium sulfate and evaporated. Crystallisation from diethyl ether. M.p. 133-135° C.

Workup

  1. customAfter evaporating the pyridine
  2. customthe residue is partitioned between ethyl acetate and 1N hydrochloric acid
  3. dry with materialThe ethyl acetate solution is dried over magnesium sulfate
  4. customevaporated
  5. customCrystallisation from diethyl ether

Sources & evidence

ORD record
ord-650e704fb437477ea75f0bcf268b4f24
Source dataset
uspto-grants-2009_05
Patent number
US07531540B2

Reaction notes

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