Sodium Hydroxide → HCID 71609447, compound

HRID 526362Notes

Reaction equation

HRID 526362 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:18]([NH:24][C:25]([C@@H:27]2[CH2:32][CH2:31][CH2:30][N:29]([C:33](=[O:49])[CH2:34][CH2:35][CH:36]3[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:38][CH2:37]3)[CH2:28]2)=[O:26])[CH2:19][C:20]([O:22]C)=[O:21])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][F:17])=[CH:10][CH:9]=2)[CH:7]=1.[OH-].[Na+]>O1CCCC1.O>[C:45]([O:44][C:42]([N:39]1[CH2:38][CH2:37][CH:36]([CH2:35][CH2:34][C:33]([N:29]2[CH2:30][CH2:31][CH2:32][C@@H:27]([C:25]([NH:24][CH:18]([C:4]3[CH:5]=[C:6]([C:8]4[CH:9]=[CH:10][C:11]([O:14][CH2:15][CH2:16][F:17])=[CH:12][CH:13]=4)[CH:7]=[C:2]([F:1])[CH:3]=3)[CH2:19][C:20]([OH:22])=[O:21])=[O:26])[CH2:28]2)=[O:49])[CH2:41][CH2:40]1)=[O:43])([CH3:48])([CH3:47])[CH3:46]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 71609446HCID 71609446, compound

Product 1

HCID 71609447HCID 71609447, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

220 mg (0.32 mmol) tert-butyl 4-{3-[(3R)-3-({1-[5-fluoro-4′-(2-fluoroethoxy)biphenyl-3-yl]-3-methoxy-3-oxopropyl}carbamoyl)piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate were dissolved in 10.4 ml tetrahydrofurane. 3.85 ml (0.39 mmol) 0.1N sodium hydroxide solution were added. The mixture was stirred at room temperature for 20 hours, diluted with water and a small amount of 1N sodium hydroxide solution and extracted with ethyl acetate. The aqueous layer was brought to pH=4.5 with 10% aqueous citric acid solution and extracted with dichloromethane and dichloromethane/2-propanol 8/2. The organic layer was dried over sodium sulfate and concentrated in vacuum to give 150 mg (70%) 3-({[(3R)-1-{3-[1-(tert-butoxycarbonyl)piperidin-4-yl]propanoyl}piperidin-3-yl]carbonyl}amino)-3-[5-fluoro-4′-(2-fluoroethoxy)biphenyl-3-yl]propanoic acid.

Workup

  1. extractiona small amount of 1N sodium hydroxide solution and extracted with ethyl acetate
  2. extractionextracted with dichloromethane and dichloromethane/2-propanol 8/2
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-f99ea618eabc4d3db21135a7718b27f2
Source dataset
uspto-grants-2016_05
Patent number
US09345793B2

Reaction notes

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