Hydrochloric Acid → HCID 67097869, compound

HRID 2078647Notes

Reaction equation

HRID 2078647 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]1([NH:34][C:35]2[CH:36]=[C:37](B(O)O)[CH:38]=[CH:39][C:40]=2[C:41]([NH:43][S:44]([CH2:47][CH2:48][CH2:49][OH:50])(=[O:46])=[O:45])=[O:42])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.C(=O)([O-])[O-].[Na+].[Na+].Cl>C1(C)C=CC=CC=1.C(O)C.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].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(OCC)(=O)C>[CH:28]1([NH:34][C:35]2[CH:36]=[C:37]([C:18]3[CH:19]=[CH:20][C:15]([O:14][CH2:13][CH2:12][N:4]([CH2:3][C@H:2]([OH:1])[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[CH:16][CH:17]=3)[CH:38]=[CH:39][C:40]=2[C:41]([NH:43][S:44]([CH2:47][CH2:48][CH2:49][OH:50])(=[O:46])=[O:45])=[O:42])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 67097763HCID 67097763, compoundHCID 67098032HCID 67098032, compound

Product 1

HCID 67097869HCID 67097869, compoundYield 35.3%

Reagents, catalysts & solvents 5

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of tert-butyl [(2R)-2-hydroxy-2-phenylethyl][2-(4-iodophenoxy)ethyl]carbamate (250 mg) and [3-(cyclohexylamino)-4-[[[(3-hydroxypropyl)sulfonyl]amino]-carbonyl]phenyl]boronic acid (258 mg) in toluene (3.0 ml) and ethanol (750 μl) were added 1,1′-bis(diphenylphosphino)ferrocene (29 mg), sodium carbonate aqueous solution (2M, 830 μl) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (38 mg) at room temperature under nitrogen and stirred at 75° C. for 2 hours. The reaction mixture was poured into 0.5N hydrochloric acid (20 ml) and ethyl acetate (20 ml), added active carbon and stirred at room temperature for 30 minutes. The mixture was filtered and separated the organic layer. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified with silica gel column chromatography to give tert-butyl [2-[[3′-(cyclohexylamino)-4′-[[[(3-hydroxypropyl)sulfonyl]amino]carbonyl]-4-biphenylyl]oxy]ethyl][(2R)-2-hydroxy-2-phenylethyl]-carbamate (127 mg).

Workup

  1. additionadded active carbon
  2. stirringstirred at room temperature for 30 minutes
  3. filtrationThe mixture was filtered
  4. customseparated the organic layer
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-8a9bc0c587574915a16d92b0bd4590e4
Source dataset
uspto-grants-2011_04
Patent number
US07928264B2

Reaction notes

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