Dichloromethane → HCID 69537328, compound

HRID 2220420Notes

Reaction equation

HRID 2220420 reaction equation
[OH:1][C@H:2]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:3][N:4]([CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18](I)=[CH:17][CH:16]=1)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[CH:28]([O:31][C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][C:37]=1[C:38]([NH:40][S:41]([CH3:44])(=[O:43])=[O:42])=[O:39])([CH3:30])[CH3:29].ClCCl.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(O)C.C1(C)C=CC=CC=1>[OH:1][C@H:2]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:3][N:4]([CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:34]2[CH:35]=[CH:36][C:37]([C:38]([NH:40][S:41]([CH3:44])(=[O:43])=[O:42])=[O:39])=[C:32]([O:31][CH:28]([CH3:30])[CH3:29])[CH:33]=2)=[CH:17][CH:16]=1)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 67097763HCID 67097763, compoundHCID 69103532HCID 69103532, compound

Product 1

HCID 69537328HCID 69537328, compoundYield 8%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

In a reaction vessel were added tert-butyl [(2R)-2-hydroxy-2-phenylethyl][2-(4-iodophenoxy)ethyl]carbamate (200 mg), [3-isopropoxy-4-[[(methylsulfonyl)amino]carbonyl]-phenyl]boronic acid (150 mg), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1, 33.8 mg), toluene (3.2 ml), ethanol (0.8 ml), and 2N sodium carbonate solution (0.66 ml). The vessel was placed in a microwave and irradiation was adjusted to keep the temperature 100° C. and the reaction was performed for 2 hours. After cooling to room temperature, the mixture was quenched by the addition of 1N hydrochloric acid (1.32 ml) and partitioned between ethyl acetate (20 ml) and water (20 ml). The organic layer was separated, washed with brine (20 ml), and dried over magnesium sulfate. Filtration followed by evaporation gave a brown foam which was chromatographed on silica gel (eluent: hexane/ethyl acetate) to give tert-butyl [(2R)-2-hydroxy-2-phenylethyl]-[2-[[3′-isopropoxy-4′-[[(methylsulfonyl)amino]carbonyl]-4-biphenylyl]oxy]ethyl]carbamate (20.4 mg) as a pale yellow solid.

Workup

  1. customThe vessel was placed in a microwave and irradiation
  2. customthe temperature 100° C.
  3. customthe mixture was quenched by the addition of 1N hydrochloric acid (1.32 ml)
  4. custompartitioned between ethyl acetate (20 ml) and water (20 ml)
  5. customThe organic layer was separated
  6. washwashed with brine (20 ml)
  7. dry with materialdried over magnesium sulfate
  8. filtrationFiltration
  9. customfollowed by evaporation
  10. customgave a brown foam which
  11. customwas chromatographed on silica gel (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-69a75d1da54448278ef6eca165e939c6
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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