2-Pyrrolidone → HCID 19903229, compound

HRID 2372320Notes

Reaction equation

HRID 2372320 reaction equation
CC(C)([O-])C.[K+].[NH:7]1[CH2:11][CH2:10][CH2:9][C:8]1=[O:12].[F:13][C:14]([F:30])([F:29])[C:15]1[N:20]=[C:19]([N:21]2[CH2:28][CH2:27][C:24]3([O:26][CH2:25]3)[CH2:23][CH2:22]2)[CH:18]=[CH:17][N:16]=1>CN(C=O)C>[OH:26][C:24]1([CH2:25][N:7]2[CH2:11][CH2:10][CH2:9][C:8]2=[O:12])[CH2:27][CH2:28][N:21]([C:19]2[CH:18]=[CH:17][N:16]=[C:15]([C:14]([F:30])([F:29])[F:13])[N:20]=2)[CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 120252-PyrrolidoneHCID 23665647Potassium tert-butoxideHCID 54397840HCID 54397840, compound

Product 1

HCID 19903229HCID 19903229, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Potassium tert-butoxide (1.03 g, 9 mmol) was added to a solution of 2-pyrrolidinone (0.7 g, 7.7 mmol) in anhydrous DMF (25 mL). The mixture was stirred for 45 min at room temperature to produce a milky white precipitate. A solution of XXIX (2.0 g, 7.7 mmol) in dry DMF (6 mL) was then added and the mixture slowly turned clear as it was stirred for 18 hr. The mixture was concentrated in vacuo and the residue chromatographed on neutral alumina using ethyl acetate as the eluent to give the white solid product (0.40 g, 35%, mp: 170°-172° C.).

Workup

  1. customto produce a milky white precipitate
  2. stirringthe mixture slowly turned clear as it was stirred for 18 hr
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue chromatographed on neutral alumina

Sources & evidence

ORD record
ord-fe97003fd65b48c19cfec1896cbfefb4
Source dataset
uspto-grants-1992_03
Patent number
US05098904

Reaction notes

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