Trifluoroacetic acid → 3-(4-methanesulfonyl-benzyl)-8-((3R,4S)-4-phenyl-pyrrolidin-3-ylmethyl)-1,3,8-triaza-spiro[4.5]decane-2,4-dione

HRID 2234210Notes

Reaction equation

HRID 2234210 reaction equation
C(OC([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@@H:10]([CH2:19][N:20]2[CH2:42][CH2:41][C:23]3([NH:27][C:26](=[O:28])[N:25]([CH2:29][C:30]4[CH:35]=[CH:34][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:32][CH:31]=4)[C:24]3=[O:40])[CH2:22][CH2:21]2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:39][S:36]([C:33]1[CH:32]=[CH:31][C:30]([CH2:29][N:25]2[C:24](=[O:40])[C:23]3([CH2:22][CH2:21][N:20]([CH2:19][C@@H:10]4[C@@H:11]([C:13]5[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=5)[CH2:12][NH:8][CH2:9]4)[CH2:42][CH2:41]3)[NH:27][C:26]2=[O:28])=[CH:35][CH:34]=1)(=[O:37])=[O:38]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11628596(3S,4S)-3-[3-(4-methanesulfonyl-benzyl)-2,4-dioxo-1,3,8-triaza-spiro[4.5]dec-8-ylmethyl]-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 592970213-(4-methanesulfonyl-benzyl)-8-((3R,4S)-4-phenyl-pyrrolidin-3-ylmethyl)-1,3,8-triaza-spiro[4.5]decane-2,4-dioneYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

83 mg (0.139 mmol) of (3S,4S)-3-[3-(4-methanesulfonyl-benzyl)-2,4-dioxo-1,3,8-triaza-spiro[4.5]dec-8-ylmethyl]-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester was dissolved in 3 mL of DCM and 1 mL of TFA and the solution was stirred overnight. The mixture was then evaporated to dryness and the residue was redissolved in 2 mL of toluene and evaporated again at 40° C. The crude compound was then dissolved in 5 mL of 5% methanol in DCM and filtered through a ChemElute™ loaded with 1 mL of 2 M NaOH. The filtrate was evaporated to yield 3-(4-methanesulfonyl-benzyl)-8-((3R,4S)-4-phenyl-pyrrolidin-3-ylmethyl)-1,3,8-triaza-spiro[4.5]decane-2,4-dione (52.1 mg, 76%).

Workup

  1. customThe mixture was then evaporated to dryness
  2. dissolutionthe residue was redissolved in 2 mL of toluene
  3. customevaporated again at 40° C
  4. dissolutionThe crude compound was then dissolved in 5 mL of 5% methanol in DCM
  5. filtrationfiltered through a ChemElute™
  6. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-4c1ded33763a47d29da465307a9a6e50
Source dataset
uspto-grants-2010_05
Patent number
US07709642B2

Reaction notes

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