Thioacetamide → HCID 11710687, compound

HRID 273182Notes

Reaction equation

HRID 273182 reaction equation
Br[CH2:2][C:3]([C@H:5]1[CH2:9][N:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=3)=[CH:12][CH:11]=2)[C:7](=[O:25])[CH2:6]1)=O.[C:26]([NH2:29])(=[S:28])[CH3:27]>O1CCCC1>[F:24][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[CH2:17][O:16][C:13]1[CH:12]=[CH:11][C:10]([N:8]2[CH2:9][C@H:5]([C:3]3[N:29]=[C:26]([CH3:27])[S:28][CH:2]=3)[CH2:6][C:7]2=[O:25])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 2723949ThioacetamideHCID 86602841HCID 86602841, compound

Product 1

HCID 11710687HCID 11710687, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

(R)-4-(2-Bromo-acetyl)-1-[4-(3-fluoro-benzyloxy)-phenyl]-pyrrolidin-2-one (0.040 g, 0.098 mmol) was dissolved in tetrahydrofuran (1 ml) and thioacetamide (0.007 g, 0.098 mmol) was added and the mixture was stirred at 40° C. for 24 hours. The tetrahydrofuran was evaporated and the residue was purified by column chromatography on silica gel using at first a 1:1-mixture then a 4:1-mixture of ethyl acetate and hexane as the eluent to yield the title compound as a light yellow solid (0.030 g, 80% of theory). MS (m/e)=383.3 (M+H)+.

Workup

  1. customThe tetrahydrofuran was evaporated
  2. customthe residue was purified by column chromatography on silica gel using at first a 1

Sources & evidence

ORD record
ord-7bc6f52a2eff479b914db18a4ad4ba0b
Source dataset
uspto-grants-2008_11
Patent number
US07456210B2

Reaction notes

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