Lithium Hydroxide → HCID 18972992, compound

HRID 2394307Notes

Reaction equation

HRID 2394307 reaction equation
[OH-].[Li+].[C:3]([O:7][C:8]([NH:10][CH:11]([CH2:16][N:17]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=1)[CH3:18])[C:12]([O:14]C)=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4]>O1CCCC1.O.Cl>[C:3]([O:7][C:8]([NH:10][CH:11]([CH2:16][N:17]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=1)[CH3:18])[C:12]([OH:14])=[O:13])=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 18973009HCID 18973009, compound

Product 1

HCID 18972992HCID 18972992, compoundYield 43.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Lithium hydroxide (55 mg) was added to a solution of the product of step (a) (722 mg) in tetrahydrofuran/water (30 ml). The mixture was stirred at room temperature for 4 hours, diluted with hydrochloric acid (1M, 50 ml) and extracted with ethyl acetate (3×50 ml). The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as a colourless foam (301 mg). NMR δH (250 MHz, CDCl3) 1.43 (9H, s), 2.59 (3H, s), 2.90 (1H, m), 3.22 (1H, m), 3.77 (1H, m) 4.10 (1H, m), 4.26 (1H, m),5.67 (1H, br s) 7.24 (1H, dd, J=11.0 and 1.0 Hz), 7.68 (2H,m). m/e (CI+) 377 (MH+).

Workup

  1. extractionextracted with ethyl acetate (3×50 ml)
  2. dry with materialThe combined organic fractions were dried (MgSO4)
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e8e134c3b2fd42419b419aba8afd6f88
Source dataset
uspto-grants-1998_09
Patent number
US05811431

Reaction notes

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