Lithium Hydroxide → HCID 25099967, compound

HRID 533233Notes

Reaction equation

HRID 533233 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[O:5][CH2:6][CH2:7][CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][C:10]=1[C:18]([O:20]CC)=[O:19].[Li+].[OH-]>CO.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[O:5][CH2:6][CH2:7][CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][C:10]=1[C:18]([OH:20])=[O:19]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67317007HCID 67317007, compound

Product 1

HCID 25099967HCID 25099967, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A mixture of EXAMPLE 3B (0.035 mg) and LiOH (0.1 g) in methanol/water (1:1, 5 mL) was heated at 150° C. under microwave (CEM Discover) conditions (70 W) for 10 minutes. The reaction mixture was concentrated, diluted with water (2 mL), treated with 5 MHCl, and extracted with ethyl acetate. The extract was dried (Na2SO4), filtered and concentrated. The concentrate was purified by reverse phaseHPLC (Zorbax SB, C-18, 20% to 100% acetonitrile/water/0.1% trifluoroacetic acid). 1H NMR (400 MHz, DMSO-d6) δ 12.88 (brs, 1H), 11.40 (s, 1H), 7.63 (d, 1H), 7.39 (d, 1H), 7.24 (m, 2H), 6.92 (m, 4H), 3.97 (t, 2H), 3.20 (t, 2H), 2.05 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water (2 mL)
  3. additiontreated with 5 MHCl
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe concentrate was purified by reverse phaseHPLC (Zorbax SB, C-18, 20% to 100% acetonitrile/water/0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-f23f2d9bcdba4163a7394184ac9ac628
Source dataset
uspto-grants-2014_10
Patent number
US08853209B2

Reaction notes

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