Lithium Hydroxide → HCID 9930126, compound

HRID 1460891Notes

Reaction equation

HRID 1460891 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]=3)=[CH:13][CH:12]=2)=[C:7]([F:29])[CH:6]=1.[Li+].[OH-].ClCCl.CO.CCCCCC.C(OCC)(=O)C>O1CCCC1>[F:29][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([OH:30])=[O:2])[CH:10]=[CH:9][C:8]=1[C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:18][C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=2)=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 3939Lithium HydroxideHCID 21226129Dichloromethane methanolHCID 21226206Ethyl acetate hexaneHCID 54060521HCID 54060521, compound

Product 1

HCID 9930126HCID 9930126, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the ester (1.69 g, 4.21 mmole) of Step F, in dry tetrahydrofuran (20 mL) is treated dropwise under nitrogen with 1N-LiOH (12.6 mL) and the mixture is stirred for 3 hours at room temperature (TLC, 19:1 dichloromethane-methanol or 1:1 hexane-ethyl acetate). The solvent is removed, the residue is treated with water and neutralized (to pH 6.5) with 10% acetic acid. The acid is extracted with ethyl acetate (large volume needed) and the extracts are dried (MgSO4) and evaporated to dryness to yield an off-white solid (1.65 g, quantitative yield, m.p. 190°-193° C., dec.). Recrystallization from ethyl acetate provides a white solid (1.32 g, 80%, m.p. 195°-196° C. dec.). The analytical sample is dried in vacuo at 40° C.

Workup

  1. customThe solvent is removed
  2. additionthe residue is treated with water and neutralized (to pH 6.5) with 10% acetic acid
  3. extractionThe acid is extracted with ethyl acetate (large volume needed)
  4. dry with materialthe extracts are dried (MgSO4)
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-c73db1877a7e43baad65a9902a4ad12e
Source dataset
uspto-grants-1991_12
Patent number
US05071988

Reaction notes

Loading…