Benzoic Acid → HCID 67597759, compound

HRID 1600978Notes

Reaction equation

HRID 1600978 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C@H:16]([OH:25])[CH2:17][CH2:18][C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(O)(=O)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[C:66]([OH:71])(=[O:70])[C:67]([OH:69])=[O:68]>CCOCC>[C:66]([OH:71])(=[O:70])[C:67]([OH:69])=[O:68].[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][C@@H:16]([OH:25])[CH2:17][CH2:18][C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)=[CH:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 243Benzoic AcidHCID 971Oxalic AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 57015495HCID 57015495, compound

Product 1

HCID 67597759HCID 67597759, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Prepared according to the method described in Example 27 from (3S)-1-(3'-chlorobiphenyl-4-yl)-5-(3-pyridyl)-3-pentanol (0.137 g, Example 86), benzoic acid (0.061 g), triphenylphosphine (0.131 g) and diethyl azodicarboxylate (0.061 ml). The mixture was concentrated under reduced pressure and the residue redissolved in methanol (8 ml) and water (2 ml). Solid sodium hydroxide (0.2 g) was added and the reaction stirred for 2 hours before being poured into a solution of saturated aqueous sodium hydrogen carbonate. The mixture was extracted with ethyl acetate, the combined organic extracts dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give an oil which was converted to the oxalate salt upon treatment with oxalic acid in ether (excess) to give the title compound as a solid (0.033 g).

Workup

  1. customPrepared
  2. concentrationThe mixture was concentrated under reduced pressure
  3. dissolutionthe residue redissolved in methanol (8 ml)
  4. additionSolid sodium hydroxide (0.2 g) was added
  5. additionbefore being poured into a solution of saturated aqueous sodium hydrogen carbonate
  6. extractionThe mixture was extracted with ethyl acetate
  7. dry with materialthe combined organic extracts dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto give an oil which

Sources & evidence

ORD record
ord-50f9d5699f344c2eb18137a8a3f57791
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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