Water → HCID 69201908, 화합물

HRID 2220646노트

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HRID 2220646 반응식
C(NC(C)C)(C)C.CS(O[CH2:13][CH2:14][O:15][C:16]1[C:21]([CH3:22])=[CH:20][C:19]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:30])=[CH:25][CH:24]=2)=[CH:18][C:17]=1[CH3:39])(=O)=O.[NH2:40][C@@H:41]([CH3:63])[C@@H:42]([C:44]1[CH:45]=[CH:46][C:47]([O:55][CH2:56][C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)=[C:48]([NH:50][S:51]([CH3:54])(=[O:53])=[O:52])[CH:49]=1)[OH:43].O>CN(C)C=O.C(OCC)(=O)C>[CH2:56]([O:55][C:47]1[CH:46]=[CH:45][C:44]([C@@H:42]([OH:43])[C@@H:41]([NH:40][CH2:13][CH2:14][O:15][C:16]2[C:17]([CH3:39])=[CH:18][C:19]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([O:31][CH2:32][C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)=[O:30])=[CH:25][CH:24]=3)=[CH:20][C:21]=2[CH3:22])[CH3:63])=[CH:49][C:48]=1[NH:50][S:51]([CH3:54])(=[O:53])=[O:52])[C:57]1[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 7912DiisopropylamineHCID 23090786Benzyl 4'-(2-methanesulfonyloxy-ethoxy)-3'5'-dimethylbiphenyl-4-carboxylateHCID 69202507HCID 69202507, 화합물

생성물 1

HCID 69201908HCID 69201908, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

Methanesulfonyl chloride (0.102 mL) was added to a mixture of benzyl 4′-(2-hydroxyethoxy)-3′,5′-dimethylbiphenyl-4-carboxylate (0.381 g) and triethylamine (0.213 mL) in methylene chloride (5 mL) at room temperature with stirring. After being stirred at that temperature for 1 hr, water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to afford benzyl 4′-(2-methanesulfonyloxyethoxy)-3′,5′-dimethylbiphenyl-4-carboxylate as a crude product. Diisopropylamine (0.148 mL) was added to a mixture of the crude benzyl 4′-(2-methanesulfonyloxyethoxy)-3′,5′-dimethylbiphenyl-4-carboxylate and N-{5-[(1R,2S)-2-amino-1-hydoxy-propyl]-2-benzyloxyphenyl}methanesulfonamide (0.154 g) in N,N-dimethylformamide (2 mL), and the mixture was stirred at 80° C. overnight. Water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: methylene chloride/methanol=30/1-20/1) to afford the title compound (0.074 g).

후처리

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: methylene chloride/methanol=30/1-20/1)

출처 및 근거

ORD 기록
ord-efab0e18371c47b2bdc3b7405f6251de
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07417169B2

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