Lithium Hydroxide → HCID 68675946, compound

HRID 1993068Notes

Reaction equation

HRID 1993068 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:39])[CH:6]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]2[CH:24]=[C:25]([C:29]3[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=3)[CH:26]=[CH:27][CH:28]=2)=[CH:17][CH:16]=1)[CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]>CO.C1COCC1.O>[C:11]([O:10][C:8](=[O:9])[CH2:7][CH:6]([C:15]1[CH:16]=[CH:17][C:18]([O:21][CH2:22][C:23]2[CH:24]=[C:25]([C:29]3[CH:34]=[CH:33][C:32]([C:35]([F:37])([F:38])[F:36])=[CH:31][CH:30]=3)[CH:26]=[CH:27][CH:28]=2)=[CH:19][CH:20]=1)[C:5]([OH:39])=[O:4])([CH3:14])([CH3:12])[CH3:13]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68675115HCID 68675115, compound

Product 1

HCID 68675946HCID 68675946, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Lithium hydroxide (121 mg, 5 mmol) was added to a solution of 50.2 in MeOH/THF/H2O (1:1:1, 90 mL). The resulting mixture was stirred at room temperature overnight. The organic solvent was removed under reduced pressure. The reaction mixture was extracted with dichloromethane (10 mL×3). The organic extracts were combined, dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified via flash chromatography (50% ethyl acetate in hexanes) to yield acid 50.3 (860 mg). MS ESI (pos.) m/e: 523 (M+Na). 1H NMR (400 MHz) (CDCl3) δ 7.72 (4H, s); 7.67 (1H, s); 7.59-7.47 (3H, m); 7.29-7.25 (2H, m); 6.98-6.97 (2H, m); 5.14 (2H, s); 4.04-4.0 (1H, m); 3.1-3.053 (1H, m); 2.64-2.60 (1H, m); 1.4 (9H, s).

Workup

  1. customThe organic solvent was removed under reduced pressure
  2. extractionThe reaction mixture was extracted with dichloromethane (10 mL×3)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified via flash chromatography (50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-1f8b76ea4074495a8447ae0ab319935a
Source dataset
uspto-grants-2010_01
Patent number
US07649110B2

Reaction notes

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