2-Chloro-4-isocyanato-1-(trifluoromethyl)benzene → HCID 67074627, compound

HRID 2095568Notes

Reaction equation

HRID 2095568 reaction equation
[OH:1][C@@H:2]([CH2:12][C:13]([N:15]1[CH2:22][CH2:21][C:18]2([CH2:20][CH2:19]2)[C@H:17]([OH:23])[CH2:16]1)=[O:14])[CH2:3][N:4]1[CH2:9][CH2:8][NH:7][C@@H:6]([CH3:10])[C:5]1=[O:11].[Cl:24][C:25]1[CH:30]=[C:29]([N:31]=[C:32]=[O:33])[CH:28]=[CH:27][C:26]=1[C:34]([F:37])([F:36])[F:35]>>[Cl:24][C:25]1[CH:30]=[C:29]([NH:31][C:32]([N:7]2[CH2:8][CH2:9][N:4]([CH2:3][C@@H:2]([OH:1])[CH2:12][C:13]([N:15]3[CH2:22][CH2:21][C:18]4([CH2:19][CH2:20]4)[C@H:17]([OH:23])[CH2:16]3)=[O:14])[C:5](=[O:11])[C@@H:6]2[CH3:10])=[O:33])[CH:28]=[CH:27][C:26]=1[C:34]([F:37])([F:36])[F:35]

Participants

3

Reactant 2

HCID 143684972-Chloro-4-isocyanato-1-(trifluoromethyl)benzene2×HCID 67074048HCID 67074048, compound2×

Product 1

HCID 67074627HCID 67074627, compoundYield 36%

Procedure

In analogy to the procedure described in Example 30, (S)—(S)-1-[2-hydroxy-4-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-4-oxo-butyl]-3-methyl-piperazin-2-one (intermediate 25) and 1.2 eq. of 2-chloro-4-isocyanato-1-trifluoromethyl-benzene (intermediate 16) gave the titled compound in 36% yield as white powder. MS: 547.19 (MH+, Cl).

Sources & evidence

ORD record
ord-4dd5abca3a7d450998a397e1b1ff4fdf
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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