Hydrochloric Acid → HCID 15592211, compound

HRID 1381719Notes

Reaction equation

HRID 1381719 reaction equation
[Cl:1][C:2]1[CH:13]=[C:12]([C:14](=[O:32])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH:11]=[CH:10][C:3]=1[C:4]([O:6]C(C)C)=[O:5].O1CCCC1.O.[OH-].[Li+].Cl>C(O)(C)C.O>[Cl:1][C:2]1[CH:13]=[C:12]([C:14](=[O:32])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH:11]=[CH:10][C:3]=1[C:4]([OH:6])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 21276535HCID 21276535, compound

Product 1

HCID 15592211HCID 15592211, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Procedure

The product from Example 10 (270 mg) was suspended in 10 ml of isopropyl alcohol and warmed. 20 ml of tetrahydrofuran was added. 200 mg of lithium hydroxide monohydrate in 3 ml of water was added followed by an additional 5 ml of water. The reaction mixture was stirred at room temperature for about 20 hours and 20 ml of 10% hydrochloric acid was added. The organic solvents were removed using a rotary evaporator and the residue was extracted with two 50 ml portions of ethyl ether. The ether extracts were combined, dried over sodium sulfate, filtered and the solvent removed under a nitrogen gas stream. The product is a white solid identical with the product disclosed in Example 15 in U.S. Pat. No. 4,469,885.

Workup

  1. temperaturewarmed
  2. customThe organic solvents were removed
  3. customa rotary evaporator
  4. extractionthe residue was extracted with two 50 ml portions of ethyl ether
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent removed under a nitrogen gas stream

Sources & evidence

ORD record
ord-eb583930d6984bd7a609ab8c3948e467
Source dataset
uspto-grants-1989_02
Patent number
US04803294

Reaction notes

Loading…