Acetic Acid → HCID 68546803, compound

HRID 2243551Notes

Reaction equation

HRID 2243551 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:15][C@@H:16]([CH3:26])[C@@H:17]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[OH:18].[CH:27]([C:30]1[CH:31]=[C:32]([C:40]2[CH:45]=[C:44]([CH3:46])[C:43]([O:47][CH2:48][C:49](=O)[CH3:50])=[C:42]([CH3:52])[CH:41]=2)[CH:33]=[CH:34][C:35]=1[C:36]([O:38][CH3:39])=[O:37])([CH3:29])[CH3:28].C(O)(=O)C>O1CCCC1>[OH:18][C@H:17]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[C@@H:16]([NH:15][CH:49]([CH3:50])[CH2:48][O:47][C:43]1[C:42]([CH3:52])=[CH:41][C:40]([C:32]2[CH:33]=[CH:34][C:35]([C:36]([O:38][CH3:39])=[O:37])=[C:30]([CH:27]([CH3:28])[CH3:29])[CH:31]=2)=[CH:45][C:44]=1[CH3:46])[CH3:26]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 6931143P-HydroxynorephedrineHCID 23090746Methyl 3-isopropyl-3',5'-dimethyl-4'-(2-oxopropoxy)biphenyl-4-carboxylate

Product 1

HCID 68546803HCID 68546803, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium triacetoxyborohydride (0.23 g) was added to a mixture of 4-((1R,2S)-2-amino-1-hydroxypropyl)phenol (0.082 g), methyl 3-isopropyl-3′,5′-dimethyl-4′-(2-oxo-propoxy)biphenyl-4-carboxylate (0.17 g) and acetic acid (0.03 mL) in tetra hydrofuran (2.5 mL) at room temperature with stirring, and the mixture was stirred at 50° C. for 4 hrs. After being cooled to room temperature, the reaction mixture was partitioned between a saturated aqueous solution of sodium bicarbonate and ethyl acetate. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: methylene chloride/methanol=9/1) followed by aminopropyl silica gel column chromatography (eluent: hexane/ethyl acetate=4/1) to afford methyl 4′-{(2RS)-2-[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)1-methylethylamino]propoxy}-3-isopropyl-3′,5′-dimethylbiphenyl-4-carboxylate (0.074 g).

Workup

  1. stirringthe mixture was stirred at 50° C. for 4 hrs
  2. customthe reaction mixture was partitioned between a saturated aqueous solution of sodium bicarbonate and ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: methylene chloride/methanol=9/1)

Sources & evidence

ORD record
ord-bb0f07d3ef6b45c9a1a39d83178c2d8c
Source dataset
uspto-grants-2010_03
Patent number
US07674938B2

Reaction notes

Loading…