4-(Trifluoromethyl)phenyl 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 (4-trifluoromethyl-phenyl)-amide

HRID 2095560Notes

Reaction equation

HRID 2095560 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.[F:23][C:24]([F:35])([F:34])[C:25]1[CH:30]=[CH:29][C:28]([N:31]=[C:32]=[O:33])=[CH:27][CH:26]=1>>[F:23][C:24]([F:34])([F:35])[C:25]1[CH:26]=[CH:27][C:28]([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:29][CH:30]=1

Participants

3

Reactant 2

HCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 67074162HCID 67074162, compound2×

Product 1

HCID 52913245(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 (4-trifluoromethyl-phenyl)-amideYield 32%

Procedure

In analogy to the procedure described in Example 25, (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 4-(trifluoromethyl)phenyl isocyanate gave the titled compound in 32% yield as white foam. MS: 497.2 (MH+).

Sources & evidence

ORD record
ord-c62d428fbf3b4eecbf996b60ef766973
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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