Oxalic Acid → HCID 67598368, compound

HRID 1600971Notes

Reaction equation

HRID 1600971 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C@H:10]([OH:19])[CH2:11][CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:26][C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=1.[C:36]([OH:41])(=[O:40])[C:37]([OH:39])=[O:38]>CCOCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C.O.C1(C)C=CC=CC=1>[C:36]([OH:41])(=[O:40])[C:37]([OH:39])=[O:38].[Cl:26][C:27]1[CH:32]=[C:31]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C@H:10]([OH:19])[CH2:11][CH2:12][C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)=[CH:4][CH:3]=2)[CH:30]=[CH:29][CH:28]=1

Participants

10

Reactant 4

HCID 971Oxalic AcidHCID 10340Sodium CarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 57192129HCID 57192129, compound

Product 1

HCID 67598368HCID 67598368, compound

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

Prepared according to the method described in Example 33a) from toluene (5 ml), water (1 ml), (3S)-1-(4-bromophenyl)-5-(3-pyridyl)-3-pentanol (0.09 g), sodium carbonate (0.172 g), 3-chlorobenzeneboronic acid (0.05 g), ethanol (1 ml) and tetrakis(triphenylphosphine)palladium(0) (9 mg) with heating at 100° C. for 45 minutes. After work up the residue was purified by column chromatography over silica eluting with ethyl acetate to give an oil which was converted to the oxalate salt upon treatment with oxalic acid (excess) in ether to give the title compound as a solid (0.057 g).

Workup

  1. customPrepared
  2. customAfter work up the residue was purified by column chromatography over silica eluting with ethyl acetate
  3. customto give an oil which

Sources & evidence

ORD record
ord-1269d228a84d41068f1c6260234d8173
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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