Acetic Acid → HCID 66871229, compound

HRID 579651Notes

Reaction equation

HRID 579651 reaction equation
[Li+].[OH-].C([O:5][C:6]([C:8]12[CH2:25][CH:24]1[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19][CH2:18][N:17]([CH3:26])[C:16](=[O:27])[CH:15]1[CH:11]([CH2:12][CH:13]([O:28][C:29]3[C:38]4[C:33](=[C:34]([CH3:41])[C:35]([O:39][CH3:40])=[CH:36][CH:37]=4)[N:32]=[C:31]([C:42]4[CH:47]=[CH:46][CH:45]=[C:44]([CH:48]([CH3:50])[CH3:49])[N:43]=4)[CH:30]=3)[CH2:14]1)[C:10](=[O:51])[NH:9]2)=[O:7])C.C(O)(=O)C>O.CO.C1COCC1>[CH:48]([C:44]1[N:43]=[C:42]([C:31]2[CH:30]=[C:29]([O:28][CH:13]3[CH2:12][CH:11]4[CH:15]([C:16](=[O:27])[N:17]([CH3:26])[CH2:18][CH2:19][CH2:20][CH2:21][CH:22]=[CH:23][CH:24]5[C:8]([C:6]([OH:7])=[O:5])([NH:9][C:10]4=[O:51])[CH2:25]5)[CH2:14]3)[C:38]3[C:33](=[C:34]([CH3:41])[C:35]([O:39][CH3:40])=[CH:36][CH:37]=3)[N:32]=2)[CH:47]=[CH:46][CH:45]=1)([CH3:50])[CH3:49]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 66871634HCID 66871634, compound

Product 1

HCID 66871229HCID 66871229, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

A solution LiOH (40 mg) in water (1.5 mL) was added to a solution of 17-[2-(6-isopropyl-2-pyridyl)-7-methoxy-8-methylquinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acid ethyl ester (112, 220 mg, 0.33 mmol) in a mixture of MeOH (3 mL) and THF (1 mL). The resulting solution was successively heated to 55° C. for 3 h, then stirred at room temperature for 5 h. Then, the pH of the reaction mixture was adjusted to pH 6 with acetic acid and water (3 mL) was added. The resulting solution was extracted with CHCl3. Then, the organic layer was dried (Na2SO4), filtered and evaporated to give 200 mg (95%) of the title compound 113 as a white powder: m/z=641 (M+H)+.

Workup

  1. additionwas added
  2. extractionThe resulting solution was extracted with CHCl3
  3. dry with materialThen, the organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-1981feb976d844b7a491240345ae1282
Source dataset
uspto-grants-2015_05
Patent number
US09040562B2

Reaction notes

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