2-Chloro-4-isocyanato-1-(trifluoromethyl)benzene → (S)-4-[4-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-3,3-dimethyl-4-oxo-butyl]-2-methyl-3-oxo-piperazine-1-carboxylic acid (3-chloro-4-trifluoromethyl-phenyl)-amide

HRID 2095569Notes

Reaction equation

HRID 2095569 reaction equation
[OH:1][C@@H:2]1[CH2:9][N:8]([C:10](=[O:24])[C:11]([CH3:23])([CH3:22])[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:25][C:26]1[CH:31]=[C:30]([N:32]=[C:33]=[O:34])[CH:29]=[CH:28][C:27]=1[C:35]([F:38])([F:37])[F:36]>>[Cl:25][C:26]1[CH:31]=[C:30]([NH:32][C:33]([N:17]2[CH2:18][CH2:19][N:14]([CH2:13][CH2:12][C:11]([CH3:23])([CH3:22])[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:24])[C:15](=[O:21])[C@@H:16]2[CH3:20])=[O:34])[CH:29]=[CH:28][C:27]=1[C:35]([F:38])([F:37])[F:36]

Participants

3

Reactant 2

HCID 143684972-Chloro-4-isocyanato-1-(trifluoromethyl)benzene2×HCID 67074651(S)-1-[4-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-3,3-dimethyl-4-oxo-butyl]-3-methyl-piperazin-2-one2×

Product 1

HCID 58232158(S)-4-[4-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-3,3-dimethyl-4-oxo-butyl]-2-methyl-3-oxo-piperazine-1-carboxylic acid (3-chloro-4-trifluoromethyl-phenyl)-amideYield 53%

Procedure

In analogy to the procedure described in Example 30, (S)-1-[4-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-3,3-dimethyl-4-oxo-butyl]-3-methyl-piperazin-2-one (intermediate 28) and 1.2 eq. of 2-chloro-4-isocyanato-1-trifluoromethyl-benzene (intermediate 16) gave the titled compound in 53% yield as off-white foam. MS: 559.23 (MH+, Cl).

Sources & evidence

ORD record
ord-4d5e5cf957894c209f7240a4a17a906d
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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