Diisopropylethylamine → HCID 19705462, compound

HRID 727575Notes

Reaction equation

HRID 727575 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]([C:12]1([C:26]([CH3:28])=[CH2:27])[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]1=[O:25])[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].C(N(C(C)C)CC)(C)C.[F:38][C:39]1[CH:40]=[C:41]([CH:45]=[CH:46][C:47]=1[F:48])[C:42](Cl)=[O:43]>C(Cl)Cl.CCOC(C)=O>[F:38][C:39]1[CH:40]=[C:41]([CH:45]=[CH:46][C:47]=1[F:48])[C:42]([NH:1][CH2:2][CH2:3][CH:4]([C:12]1([C:26]([CH3:28])=[CH2:27])[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:13]1=[O:25])[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])=[O:43]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27245193,4-Difluorobenzoyl chlorideHCID 19705530HCID 19705530, compound

Product 1

HCID 19705462HCID 19705462, compoundYield 137%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A cold (0° C.) solution of tert-butyl α-(2-aminoethyl)-2-oxo-1-(2-phenylethyl)-3-(propen-2-yl)-3-pyrrolidineacetate (1.93 g, 4.99 mmol) in dry CH2Cl2 (20 mL) is treated with diisopropylethylamine (1.04 mL, 5.99 mmol) and 3,4-difluorobenzoyl chloride (691 μL, 5.49 mmol). The solution is allowed to warm to room temperature, stirring under N2 overnight. The solution is diluted with EtOAc (100 mL) and washed with 1N HCl (25 mL), 1N NaOH (25 mL), and brine (25 mL). The organic layer is dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure to give 3.60 g of a brown oil. The oil is purified by silica gel chromatography (50 g SG; 25% EtOAc/hexane) to provide 2.10 g (80%) of the title compound as a yellow, amorphous solid:

Workup

  1. washwashed with 1N HCl (25 mL), 1N NaOH (25 mL), and brine (25 mL)
  2. dry with materialThe organic layer is dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d197421396d0417f91f2c62444f8ee8b
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

Loading…