4-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbaldehyde → (+)-(trans)-2-{4-[({4-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)amino]phenyl}cyclopropanecarboxylic acid

HRID 1173013

反応式

HRID 1173013 の反応式
C([O:3][C:4]([C@@H:6]1[CH2:8][C@H:7]1[C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1)=[O:5])C.[CH3:16][C:17]1[N:18]=[C:19]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)[S:20][C:21]=1[CH:22]=O>>[CH3:16][C:17]1[N:18]=[C:19]([C:24]2[CH:25]=[CH:26][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:28][CH:29]=2)[S:20][C:21]=1[CH2:22][NH:15][C:12]1[CH:11]=[CH:10][C:9]([C@@H:7]2[CH2:8][C@H:6]2[C:4]([OH:3])=[O:5])=[CH:14][CH:13]=1

参加物

3

反応物 2

HCID 27828994-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbaldehydeHCID 68767952rac-ethyl (1R,2R)-2-(4-aminophenyl)cyclopropane-1-carboxylate

生成物 1

HCID 11487291(+)-(trans)-2-{4-[({4-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)amino]phenyl}cyclopropanecarboxylic acid収率 25%

実験手順

Experimental procedure analogous to that described for synthesis of compounds III-2a and III-3a but instead using (+)-(trans)-ethyl-2-(4-aminophenyl)cyclopropanecarboxylate (III-1b) (0.61 g, 2.97 mmol) and 4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbaldehyde to give 0.30 g (25% yield) of pure title compound as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.98 (d, J=7.87 Hz, 2H), 7.65 (d, J=8.24 Hz, 2H), 6.97 (d, J=8.42 Hz, 2H), 6.60 (d, J=8.61 Hz, 2H), 4.46 (s, 2H), 2.51 (m, 1H), 2.50 (s, 3H), 1.79 (m, 1H), 1.59 (m, 1H), 1.35 (m, 1H). ES-MS m/z 432 (MH+). [α]25,D=+128° (chloroform, c=3.8). Product was determined to be 96% ee by chiral SFC according to Method 2.

出典と根拠

ORDレコード
ord-3c0bca39bd524fceb066640a4bfdc49a
出典データセット
uspto-grants-2010_11
特許番号
US07834013B2

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