Chlorosuccinimide → HCID 123697877, compound

HRID 84973Notes

Reaction equation

HRID 84973 reaction equation
[CH2:1]1[C@@H:10]2[C@H:4]([CH2:5][CH2:6][NH:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=32)[CH2:3][N:2]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].[Cl:22]N1C(=O)CCC1=O>CN(C)C=O>[Cl:22][C:14]1[C:8]2[NH:7][CH2:6][CH2:5][C@@H:4]3[CH2:3][N:2]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:1][C@H:10]3[C:9]=2[CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 123902436HCID 123902436, compound

Product 1

HCID 123697877HCID 123697877, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of Example 389B (172 mg, 0.60 mmol) in N,N-dimethylformamide (1 mL) was added N-chlorosuccinimide (80 mg, 0.60 mmol). The mixture was heated at 50° C. for 2 hours and purified by reversed phase HPLC (0.1% trifluoroacetic acid(aq):acetonitrile) to afford the title compound with a longer retention time than that of Example 391A.

Workup

  1. custompurified by reversed phase HPLC (0.1% trifluoroacetic acid(aq):acetonitrile)

Sources & evidence

ORD record
ord-a7b1d90c6805481286628805aae946ca
Source dataset
uspto-grants-2014_09
Patent number
US08846951B2

Reaction notes

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