HCID 10988378, compound → HCID 86736405, compound

HRID 614450Notes

Reaction equation

HRID 614450 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:10]([NH:12][C@H:13]1[C:16](=[O:17])[NH:15][C@H:14]1[CH2:18][I:19])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[C:31]([O:35][CH:36]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)(=[O:34])[CH:32]=[O:33]>O1CCCC1.CCCCCC.C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][CH:9]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:10]([NH:12][C@H:13]1[C:16](=[O:17])[N:15]([CH:32]([OH:33])[C:31]([O:35][CH:36]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[O:34])[C@H:14]1[CH2:18][I:19])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 10988378HCID 10988378, compoundHCID 86736403HCID 86736403, compoundHCID 178418339Butyllithium

Product 1

HCID 86736405HCID 86736405, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A suspension of 1.02 g (2.21 mmol) of product from Example 21 in 22 ml of dry tetrahydrofuran is stirred under argon with cooling to -78° and 1.24 ml (2.44 mmol) of a 1.97M n-butyllithium in hexane solution is added. The mixture is stirred for 30 minutes at -78° while 0.66 g (2.75 mmol) of benzhydryl glyoxylate in 20 ml of toluene is dried by distilling off 12 ml of the toluene. The remaining solution is added to the reaction mixture. The resulting mixture is stirred at -78° for 1 hour and then is warmed in an ice bath to 0° for 10 minutes. The reaction is quenched by pouring into cold aqueous NaH2PO4. The mixture is extracted with ethyl acetate and the combined extracts are washed with saline. The dried solution is evaporated and the residue is taken up in carbon tetrachloride and then hexane is added to precipitate the product, 15 g (97%).

Workup

  1. temperaturewith cooling to -78°
  2. customis dried
  3. distillationby distilling off 12 ml of the toluene
  4. additionThe remaining solution is added to the reaction mixture
  5. stirringThe resulting mixture is stirred at -78° for 1 hour
  6. temperatureis warmed in an ice bath to 0° for 10 minutes
  7. customThe reaction is quenched
  8. additionby pouring into cold aqueous NaH2PO4
  9. extractionThe mixture is extracted with ethyl acetate
  10. washthe combined extracts are washed with saline
  11. customThe dried solution is evaporated
  12. additionhexane is added
  13. customto precipitate the product, 15 g (97%)

Sources & evidence

ORD record
ord-f2494b9c21ee4b6e83ae65b1e47f41d4
Source dataset
uspto-grants-1979_03
Patent number
US04144333

Reaction notes

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