3,4-Dichlorophenyl isocyanate → (S)-4-[4-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-4-oxo-butyl]-2-methyl-3-oxo-piperazine-1-carboxylic acid (3,4-dichloro-phenyl)-amide

HRID 2095556Notes

Reaction equation

HRID 2095556 reaction equation
[OH:1][C@@H:2]1[CH2:9][N:8]([C:10](=[O:22])[CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][NH:17][C@@H:16]([CH3:20])[C:15]2=[O:21])[CH2:7][CH2:6][C:3]21[CH2:5][CH2:4]2.[Cl:23][C:24]1[CH:25]=[C:26]([N:31]=[C:32]=[O:33])[CH:27]=[CH:28][C:29]=1[Cl:30]>ClCCl>[Cl:23][C:24]1[CH:25]=[C:26]([NH:31][C:32]([N:17]2[CH2:18][CH2:19][N:14]([CH2:13][CH2:12][CH2:11][C:10]([N:8]3[CH2:7][CH2:6][C:3]4([CH2:5][CH2:4]4)[C@H:2]([OH:1])[CH2:9]3)=[O:22])[C:15](=[O:21])[C@@H:16]2[CH3:20])=[O:33])[CH:27]=[CH:28][C:29]=1[Cl:30]

Participants

4

Reactant 2

HCID 76073,4-Dichlorophenyl isocyanateHCID 67074162HCID 67074162, compound2×

Product 1

HCID 67087186(S)-4-[4-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-4-oxo-butyl]-2-methyl-3-oxo-piperazine-1-carboxylic acid (3,4-dichloro-phenyl)-amideYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.050 g (0.20 mmol) of (S)-1-[4-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-4-oxo-butyl]-3-methyl-piperazin-2-one (intermediate 13) in 1 ml of dichloromethane was treated with 0.030 g (0.20 mmol) of 3,4-dichlorophenyl isocyanate. After 1 h the reaction was evaporated and purified by flash silica gel column (dichloromethane/methanol 98/2 to 9:1) to yield 0.039 g (48%) of the titled compound as white foam. MS: 495.2 (M−H−, 2Cl).

Workup

  1. customAfter 1 h the reaction was evaporated
  2. custompurified by flash silica gel column (dichloromethane/methanol 98/2 to 9:1)

Sources & evidence

ORD record
ord-6ad8f98813d4428c81a04e59194c4b8e
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

Loading…