Chlorosuccinimide → HCID 10269678, compound

HRID 1744168Notes

Reaction equation

HRID 1744168 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:18][C@@H:17]([CH3:19])[CH2:16][C@H:9]2[C:10]([NH:12][CH2:13][C:14]#[N:15])=[O:11])[CH:5]=[CH:6][CH:7]=1.[Cl:20]N1C(=O)CCC1=O>C(O)(C)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:20])=[C:4]([N:8]2[CH2:18][C@@H:17]([CH3:19])[CH2:16][C@H:9]2[C:10]([NH:12][CH2:13][C:14]#[N:15])=[O:11])[CH:3]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 86594584HCID 86594584, compound

Product 1

HCID 10269678HCID 10269678, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

To a hot (60° C.) solution of (4S)-1-(3-bromophenyl)-N-(cyanomethyl)-4-methyl-L-prolinamide (630 mg, 1.96 mmol) in isopropyl alcohol (20 mL) was added N-chlorosuccinimide and the reaction mixture was stirred at 60° C. for 2 hours. The reaction was concentrated in vacuo and the product purified by flash chromatography over silica gel (MTBE/Hex, 1/1, then 6/4, then 8/2) to afford (4S)-1-(5-bromo-2-chlorophenyl)-N-(cyanomethyl)-4-methyl-L-prolinamide.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe product purified by flash chromatography over silica gel (MTBE/Hex, 1/1

Sources & evidence

ORD record
ord-2752d0ac53744e65b0c84a374bc9f7c4
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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