Methanesulfonic Acid → 1-ethyl-3-[5-hydroxy-7-[(E)-N-methoxy-C-methylcarbonimidoyl]-1,3-benzothiazol-2-yl]urea

HRID 712289ノート

反応式

HRID 712289 の反応式
CS(O)(=O)=O.C([O:13][C:14]1[CH:15]=[C:16](/[C:29](/[CH3:33])=[N:30]/[O:31][CH3:32])[C:17]2[S:21][C:20]([NH:22][C:23]([NH:25][CH2:26][CH3:27])=[O:24])=[N:19][C:18]=2[CH:28]=1)C1C=CC=CC=1>C(Cl)Cl>[CH2:26]([NH:25][C:23]([NH:22][C:20]1[S:21][C:17]2[C:16](/[C:29](/[CH3:33])=[N:30]/[O:31][CH3:32])=[CH:15][C:14]([OH:13])=[CH:28][C:18]=2[N:19]=1)=[O:24])[CH3:27]

参加物

4

反応物 2

HCID 6395Methanesulfonic AcidHCID 872225491-ethyl-3-[7-[(E)-N-methoxy-C-methylcarbonimidoyl]-5-phenylmethoxy-1,3-benzothiazol-2-yl]urea

生成物 1

HCID 872224611-ethyl-3-[5-hydroxy-7-[(E)-N-methoxy-C-methylcarbonimidoyl]-1,3-benzothiazol-2-yl]urea収率 54%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of methanesulfonic acid (6.5 mL) in DCM (32 mL) was added to 1-[5-benzyloxy-7-[(E)-N-methoxy-C-methyl-carbonimidoyl]-1,3-benzothiazol-2-yl]-3-ethyl-urea (718 mg, 1.8 mmol) and the reaction stirred at ambient temperature for 2 h after which time LCMS indicated clean conversion to the desired product. The reaction was diluted with DCM, washed with water and the aqueous layer neutralized with saturated aqueous Na2CO3 solution and extracted with EtOAc. The organic layer was dried (MgSO4), filtered and the solvent was removed in vacuo. The crude material obtained was purified by flash chromatography on silica gel using MeOH:DCM 3:97 as the eluent to give the desired compound as an off white solid, 300 mg, 54% yield.

出典と根拠

ORDレコード
ord-8515c633a7964ccabdc53f7d2ab71c74
出典データセット
uspto-grants-2015_11
特許番号
US09181234B2

反応ノート

読み込み中…