3,4-Dichlorophenyl isocyanate → (S)-4-(3-Hydroxy-propyl)-2-methyl-3-oxo-piperazine-1-carboxylic acid (3,4-dichloro-phenyl)-amide

HRID 655530Notes

Reaction equation

HRID 655530 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]=[C:10]=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[OH:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][NH:19][C@@H:18]([CH3:22])[C:17]1=[O:23]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:19]2[CH2:20][CH2:21][N:16]([CH2:15][CH2:14][CH2:13][OH:12])[C:17](=[O:23])[C@@H:18]2[CH3:22])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 76073,4-Dichlorophenyl isocyanateHCID 66999467(S)-1-(3-Hydroxy-propyl)-3-methyl-piperazin-2-one2×

Product 1

HCID 67080598(S)-4-(3-Hydroxy-propyl)-2-methyl-3-oxo-piperazine-1-carboxylic acid (3,4-dichloro-phenyl)-amideYield 92.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,4-Dichlorophenyl isocyanate (334 mg, 1.74 mmol) was added at 0° C. to a solution of (S)-1-(3-hydroxy-propyl)-3-methyl-piperazin-2-one (intermediate 20D; 300 mg, 1.74 mmol) in tetrahydrofuran (3 ml), then after 2.5 h the reaction mixture was evaporated. Chromatography (SiO2; dichloromethane/methanol/25% aq. ammonia solution 90:10:0.25) produced the title compound (577 mg, 92%). White foam, MS (ISP)=360.1 (M+H)+.

Workup

  1. customafter 2.5 h the reaction mixture was evaporated

Sources & evidence

ORD record
ord-8906ff1503ec4aae9ca2fd37baf4a300
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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