2-Chloro-4-isocyanato-1-(trifluoromethyl)benzene → HCID 58232164, compound

HRID 2095605Notes

Reaction equation

HRID 2095605 reaction equation
C([O:8][C:9]([N:11]1[CH2:16][C@H:15]([C:17](=[O:19])[NH2:18])[N:14]([CH2:20][CH2:21][CH2:22][C:23]([N:25]2[CH2:32][CH2:31][C:28]3([CH2:30][CH2:29]3)[C@H:27]([OH:33])[CH2:26]2)=[O:24])[C:13](=[O:34])[C@@H:12]1[CH3:35])=O)C1C=CC=CC=1.[Cl:36][C:37]1[CH:42]=[C:41]([N:43]=C=O)[CH:40]=[CH:39][C:38]=1[C:46]([F:49])([F:48])[F:47]>[Pd]>[Cl:36][C:37]1[CH:42]=[C:41]([NH:43][C:9]([N:11]2[C@@H:12]([CH3:35])[C:13](=[O:34])[N:14]([CH2:20][CH2:21][CH2:22][C:23]([N:25]3[CH2:32][CH2:31][C:28]4([CH2:30][CH2:29]4)[C@H:27]([OH:33])[CH2:26]3)=[O:24])[C@@H:15]([C:17]([NH2:18])=[O:19])[CH2:16]2)=[O:8])[CH:40]=[CH:39][C:38]=1[C:46]([F:48])([F:49])[F:47]

Participants

4

Reactant 2

HCID 143684972-Chloro-4-isocyanato-1-(trifluoromethyl)benzene2×HCID 67074996HCID 67074996, compound

Product 1

HCID 58232164HCID 58232164, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In analogy to the procedure described in the example 120 step E, (2S,5R)-5-carbamoyl-4-[4-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-4-oxo-butyl]-2-methyl-3-oxo-piperazine-1-carboxylic acid benzyl ester (example 147 step B) was first deprotected using 10% palladium on charcoal and then subsequently reacted with 2-chloro-4-isocyanato-1-trifluoromethyl-benzene (intermediate 16) to give the titled compound in 73% yield as a colorless solid. MS: 574.3 (MH+, 1Cl).

Sources & evidence

ORD record
ord-6158a8a4f020448586f2729f8c7b5c02
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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