Water → HCID 19921909, compound

HRID 1648112Notes

Reaction equation

HRID 1648112 reaction equation
C([O:3][C:4](=[O:45])[CH2:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:13]([CH2:17][CH2:18][C:19]([O:21]CC)=[O:20])=[C:12]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][C:31]3[CH:41]=[CH:40][C:34]4[C:35](=[O:39])[CH2:36][CH2:37][O:38][C:33]=4[C:32]=3[CH2:42][CH2:43][CH3:44])[CH:11]=[CH:10][C:9]=2[N:8]=1)C.O1CCCC1.O.O.[OH-].[Li+]>S(=O)(=O)(O)O.CO.C(OCC)(=O)C>[O:39]=[C:35]1[C:34]2[CH:40]=[CH:41][C:31]([O:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][O:24][C:12]3[CH:11]=[CH:10][C:9]4[N:8]=[C:7]([CH2:6][CH2:5][C:4]([OH:45])=[O:3])[CH:16]=[CH:15][C:14]=4[C:13]=3[CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[C:32]([CH2:42][CH2:43][CH3:44])[C:33]=2[O:38][CH2:37][CH2:36]1

Participants

8

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 53873785HCID 53873785, compound

Product 1

HCID 19921909HCID 19921909, compoundYield 29.6%

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of 0.126 g (0.2 mmol) of 6-[[5-[(3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)oxy]pentyl]oxy]-2,5-quinolinedipropanoic acid diethyl ester from the preceding example, 2.5 mL of tetrahydrofuran and 2.5 mL of water was added 25.7 mg (0.61 mmol) of lithium hydroxide monohydrate. The mixture was stirred at room temperature for 28.5 hr, acidified with 7 drops of 3N aqueous sulfuric acid, and worked-up with ethyl acetate in the usual manner. The residue was taken up in small amount of ethyl acetate and methanol and filtered. Most of the solvent in the filtrate was evaporated and hexane was then added to induce crystallization. The title compound (33.4 mg, 29.1%) was thus obtained as a white solid, mp 123°-128° C.

Workup

  1. filtrationfiltered
  2. customMost of the solvent in the filtrate was evaporated
  3. additionhexane was then added
  4. customcrystallization

Sources & evidence

ORD record
ord-e38925301f6341b8bb4656b01a1a07e7
Source dataset
uspto-grants-1995_07
Patent number
US05434186

Reaction notes

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