Lithium Hydroxide → HCID 22501950, compound

HRID 1633980Notes

Reaction equation

HRID 1633980 reaction equation
C([O:3][C:4](=[O:41])[CH2:5][CH2:6][NH:7][C:8](=[O:40])[C:9]1[CH:14]=[CH:13][C:12]([CH:15]([NH:28][C:29]([NH:31][C:32]2[CH:37]=[C:36]([Cl:38])[CH:35]=[C:34]([Cl:39])[CH:33]=2)=[O:30])[C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]=3)=[CH:18][CH:17]=2)=[CH:11][CH:10]=1)C.[Li+].[OH-]>C1COCC1.CO>[C:22]1([C:19]2[CH:18]=[CH:17][C:16]([CH:15]([NH:28][C:29]([NH:31][C:32]3[CH:33]=[C:34]([Cl:39])[CH:35]=[C:36]([Cl:38])[CH:37]=3)=[O:30])[C:12]3[CH:13]=[CH:14][C:9]([C:8]([NH:7][CH2:6][CH2:5][C:4]([OH:41])=[O:3])=[O:40])=[CH:10][CH:11]=3)=[CH:21][CH:20]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 54063762HCID 54063762, compound

Product 1

HCID 22501950HCID 22501950, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The propionic acid ethyl ester prepared in step D was dissolved in THF (6 mL) and MeOH (3 mL). A solution of 2 M LiOH (3 mL) was then added and the reaction was stirred at room temperature for 30 minutes. The solvents were evaporated under reduced pressure. The residue was taken up in ethyl acetate and washed with 1N HCl (2×), brine (2×), dried over MgSO4, filtered, and concentrated to a syrup. Addition of hexane followed by trituration precipitated the title compound (270 mg, 0.48 mmol) as a cream colored solid.

Workup

  1. customThe solvents were evaporated under reduced pressure
  2. washwashed with 1N HCl (2×), brine (2×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to a syrup
  6. additionAddition of hexane

Sources & evidence

ORD record
ord-5578da76dc914c40a074ef59a13dc2d4
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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