Diisopropylethylamine → HCID 178491635、化合物

HRID 710296ノート

反応式

HRID 710296 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6].O[NH:14][C:15]([C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[CH:20]2)=[NH:16].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([O:7][NH:16][C:15]([C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[CH:20]2)=[NH:14])=[O:6]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 1699823-Chloro-p-anisic acidHCID 2733179PyBroPHCID 178513238HCID 178513238、化合物

生成物 1

HCID 178491635HCID 178491635、化合物収率 93.3%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of the product of Step B (0.25 g; 1.43 mmol), and the product of Step C (0.23 g; 1.31 mmol) in anhydrous THF (5 ml), PyBroP (0.67 g; 1.44 mmol) was added followed by DIPEA (0.57 ml; 3.3 mmol), with stirring, at room temperature under N2. After 1 h of stirring, the mixture was diluted to 20 ml with EtOAc, washed with saturated NH4Cl (5 ml), brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was purified by crystallization from EtOAc/hexane to give the title compound (0.42 g; 93%), as a creamy solid. 1H-NMR (CD3OD) 3.96 (s, 3H); 5.41 (s, 1H); 6.52 (d, 1H, J=3.2 Hz); 7.14 (d, 1H, J=8.7 Hz); 7.27 (d, 1H, J=3.2 Hz); 7.41-7.77 (m, 2H); 8.0 (s, 1H); 8.11 (dd, 1H, J=2; 8.7 Hz); 8.15 (d, 1H, J=2 Hz).

後処理

  1. stirringAfter 1 h of stirring
  2. washwashed with saturated NH4Cl (5 ml), brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness under reduced pressure
  6. customthe residue was purified by crystallization from EtOAc/hexane

出典と根拠

ORDレコード
ord-d9dd7e0ed20a4de39a718bcf6393fba2
出典データセット
uspto-grants-2015_11
特許番号
US09181182B2

反応ノート

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