4-Methylmorpholine → HCID 86655206、化合物

HRID 1256079ノート

反応式

HRID 1256079 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:9][O:8][B:7]([OH:10])[C:6]=2[CH:11]=1.CN1CCOCC1.Cl[S:20]([C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:35])[C:31]([F:34])([F:33])[F:32])=[CH:25][C:24]=1[CH2:36][C:37]([O:39][CH3:40])=[O:38])(=[O:22])=[O:21]>C(#N)C>[OH:10][B:7]1[C:6]2[CH:11]=[C:2]([NH:1][S:20]([C:23]3[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:35])[C:31]([F:32])([F:33])[F:34])=[CH:25][C:24]=3[CH2:36][C:37]([O:39][CH3:40])=[O:38])(=[O:21])=[O:22])[CH:3]=[CH:4][C:5]=2[CH2:9][O:8]1

参加物

5

反応物 3

HCID 79724-MethylmorpholineHCID 37701876-Aminobenzo(c)(1,2)oxaborol-1(3H)-olHCID 86655207Methyl 2-(2-(chlorosulfonyl)-5-(2,2,2-trifluoroacetamido) phenyl)acetate

生成物 1

HCID 86655206HCID 86655206、化合物収率 65.3%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

To a stirred solution of 6-amino-3H-benzo[c][1,2]oxaborol-1-ol (3.5 g, 0.024 mol, 0.9 eq) and NMM (7.9 g, 0.079 mol, 3 eq) in acetonitrile (50 mL) was added a solution of methyl 2-(2-(chlorosulfonyl)-5-(2,2,2-trifluoroacetamido) phenyl)acetate (9.4 g, 0.026 mol) in anhydrous acetonitrile (50 mL) at 0-5° C. Then the mixture was stirred at r.t overnight, the mixture was concentrated and dissolved in DCM and then washed with brine, dried and concentrated, purified by column chromatography (PE:EA 10:1˜1.5:1) to give the title compound (7.4 g, yield 60%). 1H NMR DMSO-d6 400 MHz δ11.54 (s, 1H), 10.36 (s, 1H), 9.21 (s, 1H), 7.87-7.10 (m, 6H), 4.87 (s, 2H), 4.08 (s, 2H), 3.58 (s, 3H). ESI-MS m/z 495 (M+Na+, positive); HPLC purity: 98.23% (220 nm), 99.55% (254 nm).

後処理

  1. concentrationthe mixture was concentrated
  2. dissolutiondissolved in DCM
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated
  6. custompurified by column chromatography (PE:EA 10:1˜1.5:1)

出典と根拠

ORDレコード
ord-8ac0da6d3b7140359f499d1bc5fd443f
出典データセット
uspto-grants-2013_06
特許番号
US08461134B2

反応ノート

読み込み中…