Water → methyl 6-[4-[2-[(tert-butoxycarbonyl)[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]phenyl]-2-naphthoate

HRID 2078660Notes

Reaction equation

HRID 2078660 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH2:18][C@@H:19]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=2)[OH:20])[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:36]2[CH:37]=[C:38]3[C:43](=[CH:44][CH:45]=2)[CH:42]=[C:41]([C:46]([O:48][CH3:49])=[O:47])[CH:40]=[CH:39]3)O1.C(=O)([O-])[O-].[Na+].[Na+].O>CN(C)C=O.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:13]([O:12][C:11]([N:10]([CH2:18][C@@H:19]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=1)[OH:20])[CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:36]2[CH:37]=[C:38]3[C:43](=[CH:44][CH:45]=2)[CH:42]=[C:41]([C:46]([O:48][CH3:49])=[O:47])[CH:40]=[CH:39]3)=[CH:3][CH:4]=1)=[O:17])([CH3:16])([CH3:15])[CH3:14]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 24823936HCID 24823936, compoundHCID 53217133Methyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalene-2-carboxylate

Product 1

HCID 67097731methyl 6-[4-[2-[(tert-butoxycarbonyl)[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]phenyl]-2-naphthoateYield 74.5%

Reagents, catalysts & solvents 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of tert-butyl [2-(4-bromophenyl)ethyl]-[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]carbamate (560 mg) and methyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthoate (461 mg) in N,N-dimethylformamide (5.6 ml) were added [1′,1′-bis(diphenylphosphino)ferrocene]-palladium(II) dichloride dichloromethane complex (151 mg), 1,1′-bis(diphenylphosphino)ferrocene (102 mg) and 2M sodium carbonate (2.0 ml) at room temperature, and the mixture was stirred at 80° C. for 4 hours. The resulting mixture was poured into water and the aqueous layer was extracted with ethyl acetate. The organic layer was washed successively with water three times and brine, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1) to give methyl 6-[4-[2-[(tert-butoxycarbonyl)[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]phenyl]-2-naphthoate (514 mg).

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. washThe organic layer was washed successively with water three times and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-be2974dc1ddb43d59d15add3db5206ce
Source dataset
uspto-grants-2011_04
Patent number
US07928264B2

Reaction notes

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