Acetone → Potassium 2-((3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-fluoropiperidin-1-yl)-1,3-thiazole-5-carboxylate

HRID 1948335Notes

Reaction equation

HRID 1948335 reaction equation
[OH-].[K+:2].[Cl:3][C:4]1[C:8]([Cl:9])=[C:7]([CH3:10])[NH:6][C:5]=1[C:11]([NH:13][C@@H:14]1[CH2:19][CH2:18][N:17]([C:20]2[S:21][C:22]([C:25]([OH:27])=[O:26])=[CH:23][N:24]=2)[CH2:16][C@@H:15]1[F:28])=[O:12].CC(C)=O>CO.CC(C)=O.O>[Cl:3][C:4]1[C:8]([Cl:9])=[C:7]([CH3:10])[NH:6][C:5]=1[C:11]([NH:13][C@@H:14]1[CH2:19][CH2:18][N:17]([C:20]2[S:21][C:22]([C:25]([O-:27])=[O:26])=[CH:23][N:24]=2)[CH2:16][C@@H:15]1[F:28])=[O:12].[K+:2]

Participants

6

Reactant 3

HCID 180Acetone2×HCID 14797Potassium HydroxideHCID 117187292-[(3s,4r)-4-{[(3,4-Dichloro-5-Methyl-1h-Pyrrol-2-Yl)carbonyl]amino}-3-Fluoropiperidin-1-Yl]-1,3-Thiazole-5-Carboxylic Acid

Product 1

HCID 68515353Potassium 2-((3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-fluoropiperidin-1-yl)-1,3-thiazole-5-carboxylateYield 73.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

An aqueous solution of potassium hydroxide (0.1 M, 4.75 ml, 0.475 mmol) was added to a solution of 2-((3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-fluoropiperidin-1-yl)-1,3-thiazole-5-carboxylic acid (Example 42, 200 mg, 0.475 mmol) in methanol (35 ml). The mixture was stirred for 1 h and then concentrated under reduced pressure to provide the crude salt (230 mg). The salt was dissolved in acetone/water (50 ml; 48:2) and acetone was added slowly to the stirred mixture until it became cloudy. Stirring was continued and more acetone was added very slowly over 20 min. The mixture was stored at 4° C. overnight. The solid was collected by filtration and air dried for 24 h to provide the salt (160 mg).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto provide the crude salt (230 mg)
  3. stirringStirring
  4. waitThe mixture was stored at 4° C. overnight
  5. filtrationThe solid was collected by filtration and air
  6. customdried for 24 h

Sources & evidence

ORD record
ord-78766b359163470f9c65639907fa12ce
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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