HCID 59753323, compound → HCID 86598032, compound

HRID 751761Notes

Reaction equation

HRID 751761 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:50]([O:52]CC(=O)C1C=CC=CC=1)=[O:51])[CH2:13][O:14][C:15]([C@@H:17]1[CH2:21][C@@H:20]([CH3:22])[CH2:19][N:18]1[C:23](=[O:49])[C@@H:24]([NH:26][C:27]([C@@H:29]1[CH2:34][CH2:33][CH2:32][CH2:31][N:30]1[C:35]([C@@H:37]1[CH2:41][CH2:40][CH2:39][N:38]1[C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])=[O:36])=[O:28])[CH3:25])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Zn].C(O)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:50]([OH:52])=[O:51])[CH2:13][O:14][C:15]([C@@H:17]1[CH2:21][C@@H:20]([CH3:22])[CH2:19][N:18]1[C:23](=[O:49])[C@@H:24]([NH:26][C:27]([C@@H:29]1[CH2:34][CH2:33][CH2:32][CH2:31][N:30]1[C:35]([C@@H:37]1[CH2:41][CH2:40][CH2:39][N:38]1[C:42]([O:44][C:45]([CH3:46])([CH3:47])[CH3:48])=[O:43])=[O:36])=[O:28])[CH3:25])=[O:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 59753323HCID 59753323, compound

Product 1

HCID 86598032HCID 86598032, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

5.17 g (6.1 mmol) of the phenacyl ester from example 24A are dissolved in 90 pc. aqueous acetic acid (60 ml) and treated with 2.99 g (45.8 mmol) of zinc powder. The reaction mixture is stirred at RT for 2 h. The reaction solution is filtered off through kieselguhr and washed with ethyl acetate. The organic phase is concentrated in vacuo (not to dryness), the residue is extracted by shaking with ethyl acetate and 1N hydrochloric acid, and the phases are separated. The aqueous phase is extracted with ethyl acetate, and the combined organic phases are dried over sodium sulfate, filtered and concentrated to dryness. The residue is taken up twice in toluene and evaporated in vacuo. The residue is taken up in diethyl ether, extracted by shaking with saturated aqueous sodium hydrogencarbonate solution and the aqueous phase is washed again with diethyl ether. The aqueous phase is subsequently adjusted to pH 2.7 using 5N hydrochloric acid and extracted twice with ethyl acetate. The combined organic extracts are dried over sodium sulfate, filtered and the solvent is removed in vacuo. 4.01 g (91% of th.) of the product are obtained as a hard foam.

Workup

  1. filtrationThe reaction solution is filtered off through kieselguhr
  2. washwashed with ethyl acetate
  3. concentrationThe organic phase is concentrated in vacuo (not to dryness), the residue
  4. extractionis extracted
  5. stirringby shaking with ethyl acetate and 1N hydrochloric acid
  6. customthe phases are separated
  7. extractionThe aqueous phase is extracted with ethyl acetate
  8. dry with materialthe combined organic phases are dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated to dryness
  11. customevaporated in vacuo
  12. extractionextracted
  13. stirringby shaking with saturated aqueous sodium hydrogencarbonate solution
  14. washthe aqueous phase is washed again with diethyl ether
  15. extractionextracted twice with ethyl acetate
  16. dry with materialThe combined organic extracts are dried over sodium sulfate
  17. filtrationfiltered
  18. customthe solvent is removed in vacuo
  19. custom4.01 g (91% of th.) of the product are obtained as a hard foam

Sources & evidence

ORD record
ord-89bf16fa843e419ab56a217d76467d9d
Source dataset
uspto-grants-2008_07
Patent number
US07405201B2

Reaction notes

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