Potassium Fluoride → HCID 131727340, compound

HRID 1728163Notes

Reaction equation

HRID 1728163 reaction equation
C(OC([N:8]1[C:39]2[C:34](=[CH:35][CH:36]=[C:37]([Cl:40])[CH:38]=2)[C:10]2([CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=3)[CH2:14][C:13](=[O:23])[N:12](C(OC(C)(C)C)=O)[CH:11]2[C:31](C)=[CH2:32])[C:9]1=[O:41])=O)(C)(C)C.[F-:42].[K+].FS([C:48]([F:57])(F)[C:49](O[Si](C)(C)C)=O)(=O)=O>C1(C)C=CC=CC=1>[Cl:40][C:37]1[CH:38]=[C:39]2[NH:8][C:9](=[O:41])[C:10]3([CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=[O:23])[NH:12][CH:11]3[C@@:31]3([CH3:32])[CH2:49][C:48]3([F:57])[F:42])[C:34]2=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 522689Potassium FluorideHCID 2778022Trimethylsilyl 2,2-difluoro-2-(fluorosulfonyl)acetateHCID 76568140HCID 76568140, compound

Product 1

HCID 131727340HCID 131727340, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Racemic (2′R,3R,4′S)-1′-(tert-butoxycarbonyl)-6-chloro-4′-(3-chlorophenyl)-2′-isopropenyl-2,6′-dioxospiro[indole-3,3′-piperidine]-1-carboxylic acid tert-butyl ester (100 mg, 1.6 mmol) prepared in Example 226a, catalytic amount of KF and a large amount of trimethylsilyl fluorosulfonyldifluoroacetate was dissolved in toluene (1 mL). Then the reaction tube was placed into the cavity of a focused monomode microwave reactor and the contents of the flask were irradiated at 115° C. for 30 min. The solution was concentrated and the residue was purified by Prep-TLC (CH2Cl2:CH3OH=30:1) to obtain title compound (2.6 mg) of Example 226d and (4.1 mg) of the title compound.

Workup

  1. customThen the reaction tube was placed into the cavity of a focused monomode microwave reactor
  2. customthe contents of the flask were irradiated at 115° C. for 30 min
  3. concentrationThe solution was concentrated
  4. customthe residue was purified by Prep-TLC (CH2Cl2:CH3OH=30:1)

Sources & evidence

ORD record
ord-582ae5fe89404fadb5261347641d6606
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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