1,2-Dichloroethane → (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(1-(4-nitrophenylsulfonyl)-1H-pyrrole-2-carbonyloxy)-ethyl)pyridine 1-oxide

HRID 59728ノート

反応式

HRID 59728 の反応式
[Cl:1][C:2]1[CH:3]=[N+:4]([O-:27])[CH:5]=[C:6]([Cl:26])[C:7]=1[CH2:8][C@@H:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]([F:20])[F:19])=[C:13]([O:21][CH2:22][CH:23]2[CH2:25][CH2:24]2)[CH:12]=1)[OH:10].[N+:28]([C:31]1[CH:36]=[CH:35][C:34]([S:37]([N:40]2[CH:44]=[CH:43][CH:42]=[C:41]2[C:45](O)=[O:46])(=[O:39])=[O:38])=[CH:33][CH:32]=1)([O-:30])=[O:29].C(Cl)CCl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[N+:4]([O-:27])[CH:5]=[C:6]([Cl:26])[C:7]=1[CH2:8][C@@H:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]([F:20])[F:19])=[C:13]([O:21][CH2:22][CH:23]2[CH2:25][CH2:24]2)[CH:12]=1)[O:10][C:45]([C:41]1[N:40]([S:37]([C:34]2[CH:35]=[CH:36][C:31]([N+:28]([O-:30])=[O:29])=[CH:32][CH:33]=2)(=[O:38])=[O:39])[CH:44]=[CH:43][CH:42]=1)=[O:46]

参加物

6

反応物 3

HCID 111,2-DichloroethaneHCID 71092687(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxideHCID 867038341-(4-nitrophenylsulfonyl)-1H-pyrrole-2-carboxylic acid

生成物 1

HCID 86703836(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(1-(4-nitrophenylsulfonyl)-1H-pyrrole-2-carbonyloxy)-ethyl)pyridine 1-oxide収率 27.8%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

A mixture of (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide (206 mg, 0.490 mmol), 1-(4-nitrophenylsulfonyl)-1H-pyrrole-2-carboxylic acid (Int. 5) (160 mg, 0.539 mmol), EDC (282 mg, 1.471 mmol) and DMAP (59.9 mg, 0.490 mmol) in DCM (10 ml) was stirred at RT for 24 hours. The reaction was diluted with DCM and washed with 1N HCl, sat. NaHCO3 (40 ml), and finally with brine. The organic phase was dried over sodium sulfate and the solvent was removed under vacuum; the crude was purified by preparative HPLC-Method 1 to yield (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(1-(4-nitrophenylsulfonyl)-1H-pyrrole-2-carbonyloxy)ethyl)pyridine 1-oxide (Int. 6) (95 mg, 0.136 mmol, MS/ESI+698.05 [MH]+, [αD]=−40.97, c=0.6, DCM).

後処理

  1. washwashed with 1N HCl, sat. NaHCO3 (40 ml)
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customthe solvent was removed under vacuum
  4. customthe crude was purified by preparative HPLC-Method 1

出典と根拠

ORDレコード
ord-ff499b35fd0249fda2f80b8631f1b99f
出典データセット
uspto-grants-2016_09
特許番号
US09440954B2

反応ノート

読み込み中…