Methanesulfonic Acid → 4-(4-chlorophenoxy)-N-[(6R)-1-hydroxy-7-oxo-5,6-dihydro-2H-azepin-6-yl]-N-(2-morpholin-4-ylethyl)benzenesulfonamide

HRID 1716274ノート

反応式

HRID 1716274 の反応式
C([O:8][N:9]1[CH2:15][CH:14]=[CH:13][CH2:12][C@@H:11]([N:16]([CH2:34][CH2:35][N:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)[S:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)=[CH:22][CH:21]=2)(=[O:19])=[O:18])[C:10]1=[O:42])C1C=CC=CC=1.CS(O)(=O)=O>>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([O:26][C:23]2[CH:24]=[CH:25][C:20]([S:17]([N:16]([C@@H:11]3[CH2:12][CH:13]=[CH:14][CH2:15][N:9]([OH:8])[C:10]3=[O:42])[CH2:34][CH2:35][N:36]3[CH2:37][CH2:38][O:39][CH2:40][CH2:41]3)(=[O:19])=[O:18])=[CH:21][CH:22]=2)=[CH:32][CH:31]=1

参加物

3

反応物 2

HCID 6395Methanesulfonic AcidHCID 68516379HCID 68516379、化合物

生成物 1

HCID 547524454-(4-chlorophenoxy)-N-[(6R)-1-hydroxy-7-oxo-5,6-dihydro-2H-azepin-6-yl]-N-(2-morpholin-4-ylethyl)benzenesulfonamide収率 106.1%

実験手順

To a solution of 2.83 g of N-(1-Benzyloxy-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-(R)-yl)-4-(4-chloro-phenoxy)-N-(2-morpholin-4-yl-ethyl)-benzenesulfonamide from Step B was added 35 mL of methane sulfonic acid. The reaction was stirred at room temperature for 20 hours. The reaction was then poured over ice. The aqueous layer was extracted with 100 mL of ethyl ether twice, followed by extraction of the aqueous layer with dichloromethane (4 times). The dichloromethane layers were combined and dried over Na2SO4(s). The liquids were filtered off, and solvent removal gave a light yellow film. Dilution with ethyl ether, filtration of the resulting solids, and washing with ethyl ether and hexanes followed by drying gave 2.56 g of an orange solid. MS: 522 (M+H).

後処理

  1. additionThe reaction was then poured over ice
  2. extractionThe aqueous layer was extracted with 100 mL of ethyl ether twice
  3. extractionfollowed by extraction of the aqueous layer with dichloromethane (4 times)
  4. dry with materialdried over Na2SO4(s)
  5. filtrationThe liquids were filtered off
  6. customsolvent removal
  7. customgave a light yellow film
  8. filtrationDilution with ethyl ether, filtration of the resulting solids
  9. washwashing with ethyl ether and hexanes
  10. customby drying

出典と根拠

ORDレコード
ord-b6628174bb894133beac2e953ef46724
出典データセット
uspto-grants-2010_09
特許番号
US07803793B2

反応ノート

読み込み中…