HCID 131724776, compound → HCID 87999682, compound

HRID 983515Notes

Reaction equation

HRID 983515 reaction equation
Cl[C:2](Cl)(Cl)/[C:3](=N\[H])/[O:4][CH:5]1[O:10][CH:9]([CH3:11])[CH:8]2[O:12][CH2:13][C:14](=C)[CH:7]2[CH2:6]1.[Cl:20][CH:21]1[CH:32]([CH3:33])[CH:31]2[CH:23]([C@@:24]3([CH:51]=[O:52])[CH2:36][C@H:28]4[C@@](CO)([CH2:30]2)[C@:25]3([C:40]([O:42]COC(=O)C(C)(C)C)=[O:41])[C:26]([CH:37]([CH3:39])[CH3:38])=[CH:27]4)[CH2:22]1>C(Cl)Cl.CCOCC.CO.[Cl-].[Cl-].[Zn+2]>[Cl:20][CH:21]1[CH:32]([CH3:33])[CH:31]2[CH:23]([C@@:24]3([CH:51]=[O:52])[CH2:36][C@H:28]4[C@@:2]([CH2:3][O:4][CH:5]5[O:10][C:9](=[CH2:11])[CH:8]6[O:12][CH2:13][CH2:14][CH:7]6[CH2:6]5)([CH2:30]2)[C@:25]3([C:40]([OH:42])=[O:41])[C:26]([CH:37]([CH3:38])[CH3:39])=[CH:27]4)[CH2:22]1

Participants

7

Reactant 2

HCID 131724776HCID 131724776, compoundHCID 178506526HCID 178506526, compound

Product 1

HCID 87999682HCID 87999682, compound

Reagents, catalysts & solvents 4

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of imidate 37 prepared above in CH2Cl2 (5 mL) was added 42 (16 mg, 0.033 mmol) in CH2Cl2 (1 mL), followed by ZnCl2 (0.6 mL of a 1M solution in ether, 0.6 mmol). The mixture was stirred at room temperature for 2 hours. After aqueous work-up (CH2Cl2) and purification by PTLC, about 12.6 mg of crude product 43 (•- and •-isomers) was obtained. To a solution of this crude product 43 (4 mg) in CH3OH (2 mL) was added K2CO2 (20 mg). The mixture was stirred at room temperature for about two hours. After aqueous work-up (CH2Cl2) and purification by HPLC, about 1 mg of 44 was obtained.

Workup

  1. customAfter aqueous work-up (CH2Cl2) and purification by PTLC
  2. customabout 12.6 mg of crude product 43 (•- and •-isomers) was obtained
  3. stirringThe mixture was stirred at room temperature for about two hours
  4. customAfter aqueous work-up (CH2Cl2) and purification by HPLC

Sources & evidence

ORD record
ord-e4307c16545c4d7dae646752bf165e1e
Source dataset
uspto-grants-2005_03
Patent number
US06864278B2

Reaction notes

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