Hydrochloric Acid → N-[2-Chloro-4-(4-mesylaminophenylsulphanyl)phenyl]-2-hydroxy-2-methylpropanamide

HRID 2301031노트

반응식

HRID 2301031 반응식
O.[OH-].[Li+].[Cl:4][C:5]1[CH:10]=[C:9]([S:11][C:12]2[CH:17]=[CH:16][C:15]([N:18](S(C)(=O)=O)[S:19]([CH3:22])(=[O:21])=[O:20])=[CH:14][CH:13]=2)[CH:8]=[CH:7][C:6]=1[NH:27][C:28](=[O:36])[C:29]([O:32]C(=O)C)([CH3:31])[CH3:30].Cl.C(Cl)Cl>O.CO>[Cl:4][C:5]1[CH:10]=[C:9]([S:11][C:12]2[CH:13]=[CH:14][C:15]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[CH:16][CH:17]=2)[CH:8]=[CH:7][C:6]=1[NH:27][C:28](=[O:36])[C:29]([OH:32])([CH3:31])[CH3:30]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 168937Lithium hydroxide, monohydrateHCID 22287442N-[2-Chloro-4-{4-(N,N-dimesylamino)phenylsulphanyl}phenyl]-2-acetoxy-2-methylpropanamide

생성물 1

HCID 22287414N-[2-Chloro-4-(4-mesylaminophenylsulphanyl)phenyl]-2-hydroxy-2-methylpropanamide수율 86%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매2회

실험 절차

A solution of lithium hydroxide monohydrate (0.177 g) in water (1.8 ml) was added to a stirred solution of N-{2-chloro-4-[4-(N,N-dimesylamino)phenylsulphanyl]phenyl}-2-acetoxy-2-methylpropanamide (Method 26) (0.45 g) in methanol (3.5 ml) and the mixture was stirred at ambient temperature for 4 hours. Water (3 ml) was added and the solution was acidified to pH 2-3 with 1M hydrochloric acid. DCM (20 ml) was added and the organic layer was washed with water (20 ml) and brine, then dried. Volatile material was removed by evaporation and the residue was purified by flash chromatography eluting with 30-70% ethyl acetate/hexane to give the title compound (0.30 g) as a solid. Mp 138-140° C.; NMR (CDCl3): 1.5 (s, 6H), 3.0 (s, 3H), 7.1-7.4 (m, 7H), 8.4 (d, 1H), 9.3 (s, 1H); MS (ESP−): 413; EA: found: C, 48.9; H, 4.4; N, 6.5%; C17H19ClN2O4S2 requires C, 49.2; H, 4.6; N, 6.8%.

후처리

  1. washthe organic layer was washed with water (20 ml) and brine
  2. customdried
  3. customVolatile material was removed by evaporation
  4. customthe residue was purified by flash chromatography
  5. washeluting with 30-70% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-f1948779fd3549628a717482cc224f69
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06498275B1

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