HCID 24822811, compound → HCID 24823789, compound

HRID 1823117Notes

Reaction equation

HRID 1823117 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH2:18][C@H:19]([O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][CH:3]=1.C([Li])CCC.[Si:40]([O:47][C:48]1[CH:59]=[CH:58][C:51]([C:52](N(OC)C)=[O:53])=[CH:50][CH:49]=1)([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41]>O1CCCC1.CCCCCC>[Si:40]([O:47][C:48]1[CH:59]=[CH:58][C:51]([C:52]([C:2]2[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][N:10]([CH2:18][C@H:19]([O:27][Si:28]([C:31]([CH3:34])([CH3:32])[CH3:33])([CH3:29])[CH3:30])[C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=3)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:14])[CH3:15])=[CH:6][CH:7]=2)=[O:53])=[CH:50][CH:49]=1)([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41]

Participants

6

Reactant 3

HCID 24822811HCID 24822811, compoundHCID 24823628HCID 24823628, compoundHCID 178418339Butyllithium

Product 1

HCID 24823789HCID 24823789, compoundYield 63.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

To a solution of tert-butyl N-[2-(4-bromophenyl)-ethyl]-N-[(2R)-2-[[tert-butyl(dimethyl)silyl]oxy]-2-(3-chlorophenyl)ethyl]carbamate (880 mg) in tetrahydrofuran (13 ml) was added a solution of butyllithium in hexane (1.59M, 1.07 ml) dropwise at −70° C. under nitrogen and the mixture was stirred at −70° C. for 30 minutes. To the reaction mixture was added 4-[[tert-butyl(dimethyl)silyl]oxy]-N-methoxy-N-methylbenzamide (480 mg) at −70° C., and the mixture was stirred at −70° C. for 1 hour. The mixture was allowed to warm to room temperature and partitioned between ethyl acetate and water. The organic layer was separated, washed with saturated sodium bicarbonate solution and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=10/1) to give tert-butyl N-[2-[4-[4-[[tert-butyl(dimethyl)silyl]oxy]benzoyl]phenyl]ethyl]-N-[(2R)-2-[[tert-butyl(dimethyl)silyl]oxy]-2-(3-chlorophenyl)ethyl]carbamate (710 mg).

Workup

  1. stirringthe mixture was stirred at −70° C. for 1 hour
  2. temperatureto warm to room temperature
  3. custompartitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. washwashed with saturated sodium bicarbonate solution and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-4cd9d86bd9784d64afe318167118fa5e
Source dataset
uspto-grants-2006_05
Patent number
US07037938B2

Reaction notes

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