Lithium Hydroxide → HCID 11664670, compound

HRID 1786554Notes

Reaction equation

HRID 1786554 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:10][C@H:9]([NH:11][C:12](=[O:32])[CH2:13][CH2:14][CH2:15][CH2:16][CH:17]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH2:8][N:7]1[C:33](=[O:50])[C:34]1[CH:39]=[C:38]([C:40]([CH3:43])([CH3:42])[CH3:41])[C:37]([O:44][CH3:45])=[C:36]([C:46]([CH3:49])([CH3:48])[CH3:47])[CH:35]=1)=[O:5])C.[Li+].[OH-]>C1COCC1.CO.O>[F:24][C:21]1[CH:22]=[CH:23][C:18]([CH:17]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH2:16][CH2:15][CH2:14][CH2:13][C:12]([NH:11][C@@H:9]2[CH2:8][N:7]([C:33](=[O:50])[C:34]3[CH:39]=[C:38]([C:40]([CH3:41])([CH3:42])[CH3:43])[C:37]([O:44][CH3:45])=[C:36]([C:46]([CH3:49])([CH3:48])[CH3:47])[CH:35]=3)[C@H:6]([C:4]([OH:5])=[O:3])[CH2:10]2)=[O:32])=[CH:19][CH:20]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 11707403HCID 11707403, compound

Product 1

HCID 11664670HCID 11664670, compoundYield 75.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the solution of (2S,4S)-4-[6,6-Bis-(4-fluoro-phenyl)-hexanoylamino]-1-(3,5-di-tert-butyl-4-methoxy-benzoyl)-pyrrolidine-2-carboxylic acid ethyl ester (33) (0.32 g, 0.52 mmol) in THF (15 ml), MeOH (5 ml) and water (5 ml) was added LiOH (0.1 g, 2.45 mmol), and the reaction mixture was stirred at room temperature overnight. The reaction was then concentrated under reduced pressure. The residue was neutralized with 2N HCl to pH˜2 and dissolved in ethyl acetate: water (10:1) (150 ml). The organic was washed with water (30 ml, 2×), dried over MgSO4 and evaporated to dryness. The resulting residue was purified by column chromatography using CH2Cl2: MeOH (10:1) to give 0.26 g of desired product.

Workup

  1. concentrationThe reaction was then concentrated under reduced pressure
  2. dissolutiondissolved in ethyl acetate: water (10:1) (150 ml)
  3. washThe organic was washed with water (30 ml, 2×)
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-7f009c52032d459bb8dea3aedafca017
Source dataset
uspto-grants-2009_03
Patent number
US07507760B2

Reaction notes

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