Dimethylformamide → 4-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-(s)-thiazolidine-3-carboxylic acid tert-butyl ester

HRID 1791370ノート

反応式

HRID 1791370 の反応式
CC(OC([CH:8]1[S:12][CH2:11][CH:10]([C:13]([OH:15])=O)[NH:9]1)=O)(C)C.[CH2:16](OC(Cl)=O)[CH:17]([CH3:19])[CH3:18].CN1CC[O:28]CC1.[C:31]([C:33]1[CH:34]=[C:35]([CH:40]=[CH:41][CH:42]=1)[C:36]([NH:38]O)=[NH:37])#[N:32].CN([CH:46]=[O:47])C>C1COCC1>[C:17]([O:28][C:46]([N:9]1[C@@H:10]([C:13]2[O:15][N:38]=[C:36]([C:35]3[CH:40]=[CH:41][CH:42]=[C:33]([C:31]#[N:32])[CH:34]=3)[N:37]=2)[CH2:11][S:12][CH2:8]1)=[O:47])([CH3:19])([CH3:18])[CH3:16]

参加物

7

反応物 5

HCID 6228DimethylformamideHCID 79724-Methylmorpholine2 回HCID 62365Isobutyl chloroformateHCID 220327532-[(2-Methylpropan-2-yl)oxycarbonyl]-1,3-thiazolidine-4-carboxylic acidHCID 178509779HCID 178509779、化合物

生成物 1

HCID 696193594-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-(s)-thiazolidine-3-carboxylic acid tert-butyl ester収率 20%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
120 °C

実験手順

4-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-(S)-thiazolidine-3-carboxylic acid tert-butyl ester (212 mg, 20%, yellow oil) was prepared according to the procedure in Example 25 from Boc-L-thiazolidine-4-carboxylic acid (696 mg, 2.98 mmol) with isobutylchloroformate (0.43 ml, 3.28 mmol) and N-methylmorpholine (0.36 ml, 3.28 mmol) in THF (5 ml) at 40° C. for 2 h. Then 3-cyano-N-hydroxy-benzamidine (577 mg, 3.58 mmol) and additional N-methylmorpholine (0.39 ml, 3.58 mmol) and THF (4 ml) at room temperature overnight followed by extraction of the product and addition of DMF (2 ml) and the mixture was heated at 120° C. overnight. The crude residue was purified on silica gel using 20% ethyl acetate.

後処理

  1. customThe crude residue was purified on silica gel using 20% ethyl acetate

出典と根拠

ORDレコード
ord-b04a569322c9446191de98fea4a5dc0b
出典データセット
uspto-grants-2006_07
特許番号
US07074809B2

反応ノート

読み込み中…