HCID 86760833, compound → HCID 86760832, compound

HRID 1728218Notes

Reaction equation

HRID 1728218 reaction equation
C(OC([N:8]1[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([Cl:33])[CH:31]=2)[C@@:10]2([C@H: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][C@H:11]2[C:24]([Br:26])=[CH2:25])[C:9]1=[O:34])=O)(C)(C)C>FC(F)(F)C(O)=O>[Br:26][C:24]([C@H:11]1[C@:10]2([C:27]3[C:32](=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)[NH:8][C:9]2=[O:34])[C@H:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)[CH2:14][C:13](=[O:23])[NH:12]1)=[CH2:25]

Participants

3

Reactant 1

HCID 86760833HCID 86760833, compound

Product 1

HCID 86760832HCID 86760832, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of chiral (2′R,3R,4′S)-2′-(1-bromo-vinyl)-6-chloro-4′-(3-chlorophenyl)-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-carboxylic acid tert-butyl ester (9 mg, 0.016 mmol) in trifluoroacetic acid (1 mL) was stirred at room temperature for 10 min, then concentrated in vacuo. The residue was purified by Prep-HPLC to give title compound (5.7 mg, 76%). m/z (M+H)+: 465

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by Prep-HPLC

Sources & evidence

ORD record
ord-07ed38b317594f189e9475f537ad23a4
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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