Trifluoroacetic acid → HCID 58573478, compound

HRID 931947Notes

Reaction equation

HRID 931947 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[N:8]([CH2:33][O:34]CC[Si](C)(C)C)[C:9](=[O:32])[C@:10]3([C@@H:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C@H:13]([CH2:23][C:24]([OH:26])=[O:25])[C:12](=[O:27])[N:11]3[CH2:28][CH:29]3[CH2:31][CH2:30]3)[C:5]2=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]2[N:8]([CH2:33][OH:34])[C:9](=[O:32])[C@:10]3([C@@H:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C@H:13]([CH2:23][C:24]([OH:26])=[O:25])[C:12](=[O:27])[N:11]3[CH2:28][CH:29]3[CH2:30][CH2:31]3)[C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58573626HCID 58573626, compound

Product 1

HCID 58573478HCID 58573478, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (rac) 2-((2′S,3′R,5′R)-6-chloro-3′-(3-chlorophenyl)-1′-(cyclopropylmethyl)-2,6′-dioxo-1-((2-(trimethylsilyl)ethoxy)methyl)spiro[indoline-3,2′-piperidine]-5′-yl)acetic acid (Example 62, Step K) (47 mg, 0.078 mmol) in DCM (0.8 mL) at room temperature was added 0.2 mL TFA. The reaction mixture was stirred at room temperature for 19 h before concentrating under reduced pressure. The residue was purified by flash chromatography on silica gel (eluent: 50 to 100% EtOAc in hexanes) to give the title compound.

Workup

  1. concentrationbefore concentrating under reduced pressure
  2. customThe residue was purified by flash chromatography on silica gel (eluent: 50 to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-69f47468bc8341ddae2f87a91e757983
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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