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 1716274노트

반응식

HRID 1716274 반응식
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

참가 물질

3

반응물 2

HCID 6395Methanesulfonic AcidHCID 68516379HCID 68516379, 화합물

생성물 1

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b6628174bb894133beac2e953ef46724
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07803793B2

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