Methyl acetoacetate → 2-Methyl-1-[(R)-1-(tetrahydro-furan-2-yl)methyl]-5-(2-trifluoromethoxy-phenyl)-1H-pyrrole-3-carboxylic acid ((1RS,2RS)-2-hydroxy-cyclohexyl)-amide

HRID 229866Notes

Reaction equation

HRID 229866 reaction equation
CO[C:3](=[O:8])[CH2:4][C:5](=O)[CH3:6].Br[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][C:20]([F:23])([F:22])[F:21])=O.[CH2:24]([NH2:30])[C@@H:25]1[O:29][CH2:28][CH2:27][CH2:26]1.[NH2:31][C@@H:32]1[CH2:37][CH2:36][CH2:35][CH2:34][C@H:33]1[OH:38]>>[OH:38][CH:33]1[CH2:34][CH2:35][CH2:36][CH2:37][CH:32]1[NH:31][C:3]([C:4]1[CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][C:20]([F:23])([F:22])[F:21])[N:30]([CH2:24][C@H:25]2[CH2:26][CH2:27][CH2:28][O:29]2)[C:5]=1[CH3:6])=[O:8]

Participants

5

Reactant 4

HCID 7757Methyl acetoacetateHCID 735777(1R,2R)-2-AminocyclohexanolHCID 2734124(R)-(-)-TetrahydrofurfurylamineHCID 27786842-(Trifluoromethoxy)phenacyl bromide

Product 1

HCID 116124232-Methyl-1-[(R)-1-(tetrahydro-furan-2-yl)methyl]-5-(2-trifluoromethoxy-phenyl)-1H-pyrrole-3-carboxylic acid ((1RS,2RS)-2-hydroxy-cyclohexyl)-amide

Procedure

The title compound was synthesized in analogy to example 7, using 3-oxo-butyric acid methyl ester as compound of formula R, 2-bromo-1-[2-(trifluoromethoxy)phenyl]-ethanone as compound of formula S, (R)-tetrahydrofurfurylamine as R3—(CH2)m—NH2 and trans-2-aminocyclohexanol as R1R2NH, MS (ISP) 467.5 (M+H)+.

Sources & evidence

ORD record
ord-1e52aa425deb4c839cd31422264899b0
Source dataset
uspto-grants-2009_07
Patent number
US07563910B2

Reaction notes

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