Lithium Hydroxide → HCID 57658314, compound

HRID 1667386Notes

Reaction equation

HRID 1667386 reaction equation
[NH2:1][C:2]1[N:7]([C:8]2[CH:31]=[CH:30][C:11]([O:12][CH2:13][C:14]([NH:16][C@H:17]([C:22]([O:24]C3CCCC3)=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])=[O:15])=[CH:10][CH:9]=2)[C:6](=[O:32])[CH:5]=[CH:4][C:3]=1[C:33](=[O:41])[C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1.[Li+].[OH-]>C1COCC1.O>[NH2:1][C:2]1[N:7]([C:8]2[CH:31]=[CH:30][C:11]([O:12][CH2:13][C:14]([NH:16][C@H:17]([C:22]([OH:24])=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])=[O:15])=[CH:10][CH:9]=2)[C:6](=[O:32])[CH:5]=[CH:4][C:3]=1[C:33](=[O:41])[C:34]1[CH:35]=[CH:36][C:37]([F:40])=[CH:38][CH:39]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 57658329HCID 57658329, compound

Product 1

HCID 57658314HCID 57658314, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

From Example 56. To a solution of cyclopentyl N-({4-[6-amino-5-(4-fluorobenzoyl)-2-oxopyridin-1(2H)-yl]phenoxy}acetyl)-L-leucinate (35 mg, 0.06 mmol) in THF (1 ml) and water (1 ml) was added LiOH (30 mg, 1.24 mmol, 20 eq). The mixture was stirred at room temperature for 16 hours, concentrated under reduced pressure and water (5 ml) added. The pH was adjusted to 7 using 1M HCl and the aqueous layer extracted with 1-butanol (3×5 ml). The combined organic extracts were concentrated under reduced pressure. The solid residue was triturated with Et2O, filtered and dried under reduced pressure to provide the title compound as a cream solid (11 mg, 36% yield).

Workup

  1. concentrationconcentrated under reduced pressure and water (5 ml)
  2. additionadded
  3. extractionthe aqueous layer extracted with 1-butanol (3×5 ml)
  4. concentrationThe combined organic extracts were concentrated under reduced pressure
  5. customThe solid residue was triturated with Et2O
  6. filtrationfiltered
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-22792220e38140608bf055b41e38715b
Source dataset
uspto-grants-2011_10
Patent number
US08044211B2

Reaction notes

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