(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → (2S,4R)-4-benzyl-1-(2-cyanoacetyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide

HRID 1630194ノート

反応式

HRID 1630194 の反応式
Cl.[C:2]([CH2:4][C:5]([OH:7])=O)#[N:3].[CH2:8]([C@H:15]1[CH2:19][NH:18][C@H:17]([C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)=[CH:25][CH:24]=2)=[O:21])[CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[CH2:8]([C@H:15]1[CH2:19][N:18]([C:5](=[O:7])[CH2:4][C:2]#[N:3])[C@H:17]([C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]3[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=3)=[CH:25][CH:24]=2)=[O:21])[CH2:16]1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

参加物

3

反応物 2

HCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamideHCID 866594752-Cyanoacetic acid hydrochloride

生成物 1

HCID 67010736(2S,4R)-4-benzyl-1-(2-cyanoacetyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide収率 23.3%

実験手順

Proceeding as in Example 1, but substituting 2-cyanoacetic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 129, (2S,4R)-4-benzyl-1-(2-cyanoacetyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (6.4 mg, 23.3%); Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 9.99 (s, 1H), 7.55-7.60 (m, 2H), 7.29-7.32 (m, 2H), 7.17-7.23 (m, 5H), 6.95-7.02 (m, 4H), 4.49 (m, 1H), 4.00 (m, 2H), 3.64 (m, 1H), 3.22 (m, 2H), 3.67 (m, 3H), 1.93 (m, 2H). MS (EI) for C27H24FN3O3. found 458.5 (MH+).

出典と根拠

ORDレコード
ord-71da31197da2427784d444f02e43a12b
出典データセット
uspto-grants-2014_07
特許番号
US08791102B2

反応ノート

読み込み中…