2-Chloro-4-isocyanato-1-(trifluoromethyl)benzene → (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-chloro-4-trifluoromethyl-phenyl)-amide

HRID 2095564Notes

Reaction equation

HRID 2095564 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:29]=[C:28]([N:30]=[C:31]=[O:32])[CH:27]=[CH:26][C:25]=1[C:33]([F:36])([F:35])[F:34]>>[Cl:23][C:24]1[CH:29]=[C:28]([NH:30][C:31]([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:32])[CH:27]=[CH:26][C:25]=1[C:33]([F:36])([F:35])[F:34]

Participants

3

Reactant 2

HCID 143684972-Chloro-4-isocyanato-1-(trifluoromethyl)benzene2×HCID 67074162HCID 67074162, compound2×

Product 1

HCID 67086910(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-chloro-4-trifluoromethyl-phenyl)-amideYield 83%

Procedure

In analogy to the procedure described in Example 30, (S)-1-[4-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-4-oxo-butyl]-3-methyl-piperazin-2-one (intermediate 13) and 2-chloro-4-isocyanato-1-trifluoromethyl-benzene (intermediate 16) gave the titled compound in 83% yield as white foam. MS: 531.20 (MH+, 1Cl).

Sources & evidence

ORD record
ord-0f58cfbbb83842ac867e19bc7170e323
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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