Water → HCID 67040326, compound

HRID 604537Notes

Reaction equation

HRID 604537 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11](Cl)=[O:12])=[CH:4][CH:3]=1.[C:14]([O:17][CH2:18][C@@:19]([NH:30][C:31](=[O:33])[CH3:32])([CH2:28][CH3:29])[CH2:20][CH2:21][C:22]1[N:23]([CH3:27])[CH:24]=[CH:25][CH:26]=1)(=[O:16])[CH3:15].C([O:37][CH2:38][CH3:39])(=O)C.O>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[C:14]([O:17][CH2:18][C@@:19]([NH:30][C:31](=[O:33])[CH3:32])([CH2:28][CH3:29])[CH2:20][CH2:21][C:22]1[N:23]([CH3:27])[C:24]([C:11]([O:12][C:38](=[O:37])[CH2:39][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)=[CH:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)=[CH:25][CH:26]=1)(=[O:16])[CH3:15]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 23160109HCID 23160109, compoundHCID 67040053HCID 67040053, compound

Product 1

HCID 67040326HCID 67040326, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
110 °C

Procedure

A solution of 4-dimethylaminopyridine (1.17 g, 11.8 mmol) and 4-(4-methylphenyl)butyric chloride (1.06 g, 5.90 mmol) in toluene (5 mL) was added to a solution of (2R)-1-acetoxy-2-acetylamino-2-ethyl-4-(1-methylpyrrol-2-yl)butane (444 mg, 1.60 mmol) obtained in Reference example 2 in toluene (15 mL) and the mixture was stirred at 110° C. for 72 hours. The temperature of the mixture was returned to room temperature and ethyl acetate and water were added to the reaction mixture to separate it. The thus obtained organic phase was separated, washed with water and a saturated aqueous NaCl solution and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (ethyl acetate:hexane, 3:2-2:1) to obtain the title compound (377 mg, yield: 40%).

Workup

  1. customwas returned to room temperature
  2. customto separate it
  3. customThe thus obtained organic phase was separated
  4. washwashed with water
  5. dry with materiala saturated aqueous NaCl solution and dried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel chromatography (ethyl acetate:hexane, 3:2-2:1)

Sources & evidence

ORD record
ord-f281ec75072c4c5dbdaebfe0288aea8a
Source dataset
uspto-grants-2011_03
Patent number
US07910617B2

Reaction notes

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