Hydrochloric Acid → HCID 15950100, compound

HRID 883668Notes

Reaction equation

HRID 883668 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][C:13](=[O:15])[N:12]([CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=4)[C:11]3=[O:24])[C:9](=[O:25])[N:8]([CH2:26][C:27]([O:29]C)=[O:28])[C:5]2=[CH:6][CH:7]=1.I[Si](C)(C)C.Cl.C(OCC)(=O)C>C(Cl)(Cl)Cl.C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][C:13](=[O:15])[N:12]([CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=4)[C:11]3=[O:24])[C:9](=[O:25])[N:8]([CH2:26][C:27]([OH:29])=[O:28])[C:5]2=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 85247Trimethylsilyl iodideHCID 58017135HCID 58017135, compound

Product 1

HCID 15950100HCID 15950100, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 6342AcetonitrileSolvent

Procedure

Alternatively, a solution of methyl [5-chloro-1′-(3-chlorobenzyl)-2,2′,5′-trioxospiro[indole-3,3′-pyrrolidin]-1(2H)-yl)acetate, intermediate 48, (250 mg, 0.56 mmol) in chloroforme or acetonitrile (10 ml) was treated with iodotrimethylsilane (0.31 ml, 2.24 mmol) and heated up to reflux until completion. Addition of 1.0 N HCl (10 ml), product extraction with ethyl acetate or chloroforme (3×5 ml), washing of the combined extracts with sat. sodium thiosulfate (10 ml) and drying (MgSO4) gave the title compound as in quant.yield as slightly yellow solid (75% purity by HPLC using chloroform; 68% purity by HPLC using acetonitrile). MS (ESI+): 434.3; MS (ESI−): 431.4.

Workup

  1. temperatureheated up
  2. temperatureto reflux until completion
  3. washwashing of the combined extracts with sat. sodium thiosulfate (10 ml)
  4. dry with materialdrying (MgSO4)

Sources & evidence

ORD record
ord-d4d1731a92d0450686fbb965be41d5a6
Source dataset
uspto-grants-2012_08
Patent number
US08236963B2

Reaction notes

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