HCID 76567976, compound → HCID 76568175, compound

HRID 1728150Notes

Reaction equation

HRID 1728150 reaction equation
C(OC([N:8]1[C:44]2[C:39](=[CH:40][CH:41]=[C:42]([Cl:45])[CH:43]=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])[NH:12][CH:11]2[C:24]2[CH:29]=[C:28]([I:30])[CH:27]=[CH:26][C:25]=2[O:31][Si](C(C)(C)C)(C)C)[C:9]1=[O:46])=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Cl:45][C:42]1[CH:43]=[C:44]2[NH:8][C:9](=[O:46])[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:24]3[CH:29]=[C:28]([I:30])[CH:27]=[CH:26][C:25]=3[OH:31])[C:39]2=[CH:40][CH:41]=1

Participants

3

Reactant 1

HCID 76567976HCID 76567976, compound

Product 1

HCID 76568175HCID 76568175, compound

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

Racemic (2′R,3R,4′S)-2′-[2-(tert-butyl-dimethylsilanyloxy)-5-iodo-phenyl]-6-chloro-4′-(3-chlorophenyl)-2,6′-dioxo-spiro[3H-indole-3,3′-piperidine]-1-carboxylic acid tert-butyl ester (200 mg, 0.25 mmol) was dissolved in 30% TFA/CH2Cl2 (5 mL) and the solution was stirred at rt for 2 h. The solvent was removed and the residue was partioned between water and methylene chloride. The organic layer was separated and dried with sodium sulfate and concentrated. The residue was chromatographed to give a white solid which was directly used for next step. MS (H+), 579.

Workup

  1. customThe solvent was removed
  2. customThe organic layer was separated
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was chromatographed
  6. customto give a white solid which

Sources & evidence

ORD record
ord-152195f4d0294edda271f73758b67ad7
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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