Trifluoroacetic acid → 5-[4-(Benzothiazol-2-yloxy)-benzyl]-hexahydro-pyrrolo[3,4-c]pyrrole-2-sulfonic acid amide

HRID 384528ノート

反応式

HRID 384528 の反応式
C(OC([CH:8]1[CH:12]2[CH2:13][N:14]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]4[S:25][C:26]5[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=5[N:28]=4)=[CH:19][CH:18]=3)[CH2:15][CH:11]2[CH2:10][N:9]1[S:33]([NH2:36])(=[O:35])=[O:34])=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl.CO.CS(C)=O>[S:25]1[C:26]2[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=2[N:28]=[C:24]1[O:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][N:14]2[CH2:15][CH:11]3[CH2:10][N:9]([S:33]([NH2:36])(=[O:34])=[O:35])[CH2:8][CH:12]3[CH2:13]2)=[CH:22][CH:21]=1

参加物

5

反応物 2

HCID 6422Trifluoroacetic acidHCID 86629966Tert-butoxy carbonyl-5-[4-(benzothiazol-2-yloxy)-benzyl]-hexahydro-pyrrolo[3,4-c]pyrrole-2-sulfonic acid amide

生成物 1

HCID 426005665-[4-(Benzothiazol-2-yloxy)-benzyl]-hexahydro-pyrrolo[3,4-c]pyrrole-2-sulfonic acid amide収率 70%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 22036561Dimethyl sulfoxide methanol溶媒

実験手順

To a stirred solution tert-butoxy carbonyl-5-[4-(benzothiazol-2-yloxy)-benzyl]-hexahydro-pyrrolo[3,4-c]pyrrole-2-sulfonic acid amide (108 mg, 0.20 mmol) in CH2Cl2 (5 mL) was added trifluoroacetic acid (1 mL). The homogeneous reaction mixture was allowed to stir overnight at rt. The crude reaction mixture was blown down to dryness and dissolved in CH3OH/DMSO (2:1) and purified via reverse phase preparative HPLC to afford the title compound as fluffy white powder (60 mg, 70%). MS (ESI): mass calcd. for C20H22N4O3S2, 430.6; m/z found, 431.1 [M+H]+; 1H NMR (500 MHz, CD3OD): 7.79 (d, J=8.0 Hz, 1H), 7.67 (d, J=8.1 Hz, 1H), 7.52-7.46 (m, 2H), 7.46-7.39 (m, 1H), 7.37-7.27 (m, 3H), 3.68 (s, 2H), 3.24 (dd, J=9.5, 7.0 Hz, 2H), 3.06 (dd, J=9.4, 2.6 Hz, 2H), 2.93-2.87 (m, 2H), 2.87-2.78 (m, 2H), 2.40 (dd, J=8.5, 3.6 Hz, 2H).

後処理

  1. customThe crude reaction mixture
  2. custompurified via reverse phase preparative HPLC

出典と根拠

ORDレコード
ord-b3dbeaddbbff4723b484c8d2a652b102
出典データセット
uspto-grants-2013_02
特許番号
US08367719B2

反応ノート

読み込み中…