HCID 131719364, compound → HCID 15608452, compound

HRID 1720094Notes

Reaction equation

HRID 1720094 reaction equation
C([O:10][C:11](=[O:55])[C@H:12]([C@@H:24]([CH3:54])[O:25][C:26](=[O:53])[C@H:27]([CH2:44][C:45]1[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][CH:46]=1)[N:28]([C:30](=[O:43])[C@@H:31]1[CH2:35][CH2:34][CH2:33][N:32]1[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH3:29])[NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])C(C1C=CC=CC=1)=O>[Zn].C(O)(=O)C>[C:39]([O:38][C:36]([N:32]1[CH2:33][CH2:34][CH2:35][C@H:31]1[C:30]([N:28]([CH3:29])[C@H:27]([C:26]([O:25][C@H:24]([CH3:54])[C@@H:12]([C:11]([OH:55])=[O:10])[NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])=[O:53])[CH2:44][C:45]1[CH:46]=[CH:47][C:48]([O:51][CH3:52])=[CH:49][CH:50]=1)=[O:43])=[O:37])([CH3:40])([CH3:41])[CH3:42]

Participants

4

Reactant 1

HCID 131719364HCID 131719364, compound

Product 1

HCID 15608452HCID 15608452, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

2.80 g (3.68 mmol) of (12 ) were stirred with 1.8 g of zinc powder in 20 ml of 90% strength aqueous acetic acid at RT for 4 h; undissolved zinc was filtered off, and the filtrate was concentrated under reduced pressure. The residue was partitioned between EA and 1N KHSO4. The combined organic phases were dried (MgSO4) and concentrated under reduced pressure. The remaining resin was evaporated with toluene 3 times under reduced pressure. It was then taken up in 10 ml of 1N KHCO3, the solution was extracted twice with ether, and the ether phases were back-extracted twice with H2O. EA was added to the combined aqueous phases, which were acidified with 1N KHSO4 while cooling. The mixture was extracted twice more with EA, and the combined organic solutions were dried (MgSO4) and evaporated under reduced pressure. Yield: 2.25 g (3.5 mmol, 95%).

Workup

  1. filtrationundissolved zinc was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was partitioned between EA and 1N KHSO4
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe remaining resin was evaporated with toluene 3 times under reduced pressure
  7. extractionthe solution was extracted twice with ether
  8. extractionthe ether phases were back-extracted twice with H2O
  9. additionEA was added to the combined aqueous phases, which
  10. temperaturewhile cooling
  11. extractionThe mixture was extracted twice more with EA
  12. dry with materialthe combined organic solutions were dried (MgSO4)
  13. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-461c61ba87b2453c8602e9de502385c7
Source dataset
uspto-grants-1996_04
Patent number
US05504189

Reaction notes

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