Water → HCID 69201908, compound

HRID 2220646Notes

Reaction equation

HRID 2220646 reaction equation
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

Participants

7

Reactant 4

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

Product 1

HCID 69201908HCID 69201908, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-efab0e18371c47b2bdc3b7405f6251de
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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