Hydrochloric Acid → (E)-3-(2-{3-[2-(Phenylmethoxy)phenyl]phenyl}phenyl)-N-(2-thienylsulfonyl)prop-2-enamide

HRID 1168904ノート

反応式

HRID 1168904 の反応式
[C:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[CH:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3/[CH:27]=[CH:28]/[C:29](O)=[O:30])[CH:18]=[CH:19][CH:20]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:32]1[CH:36]=[CH:35][CH:34]=[C:33]1[S:37]([NH-:40])(=[O:39])=[O:38].CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl.CC(O)=O>[C:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[CH:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3/[CH:27]=[CH:28]/[C:29]([NH:40][S:37]([C:33]3[S:32][CH:36]=[CH:35][CH:34]=3)(=[O:39])=[O:38])=[O:30])[CH:18]=[CH:19][CH:20]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 12112238(E)-3-(2-{3-[2-(Phenylmethoxy)phenyl]phenyl}phenyl)prop-2-enoic acidHCID 865853752-Thiophenesulfonylamide

生成物 1

HCID 10209488(E)-3-(2-{3-[2-(Phenylmethoxy)phenyl]phenyl}phenyl)-N-(2-thienylsulfonyl)prop-2-enamide収率 56.1%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒

実験手順

To (E)-3-(2-{3-[2-(Phenylmethoxy)phenyl]phenyl}phenyl)prop-2-enoic acid (210 mg, 0.52 mmol) of Example 2 (step 2), 2-thiophenesulfonylamide (121 mg, 0.74 mmol) and DMAP (250 mg, 2.04 mmol) in CH2Cl2 (3 mL) was added EDCI (142 mg, 0.74 mmol). After stirring at r.t. for 2 days, the reaction mixture was poured into 1N HCl (or aqueous AcOH) and extracted with EtOAc. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated. Purification by flash chromatography (Tol:EtOAc:AcOH, 1:0:0 to 20:1:0.1) and recrystallization (Hex:CH2Cl2) provided the desired material as a white solid (161 mg, 56%). 1H NMR (acetone-d6) δ 5.13 (2H, s), 6.72 (1H, d), 7.04 (1H, td), 7.1-7.2 (2H, m), 7.2-7.4 (8H, m), 7.4-7.5 (4H, m), 7.55 (1H, t), 7.62 (1H, dt), 7.7-7.8 (3H, m) and 7.92 (1H, dd).

後処理

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification
  7. customby flash chromatography (Tol:EtOAc:AcOH, 1:0:0 to 20:1:0.1) and recrystallization (Hex:CH2Cl2)

出典と根拠

ORDレコード
ord-29e2a94aa6e743d5b89d9cacfdee233d
出典データセット
uspto-grants-2003_09
特許番号
US06627656B2

反応ノート

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