Trifluoroacetic acid → [5-chloro-1'-[(5-methyl-3-phenylisoxazol-4-yl)methyl]-2,2'-dioxospiro[indole-3,3'-pyrrolidin]-1(2H)-yl]acetic acid

HRID 883670Notes

Reaction equation

HRID 883670 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([CH2:15][C:16]4[C:17]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)=[N:18][O:19][C:20]=4[CH3:21])[C:11]3=[O:28])[C:9](=[O:29])[N:8]([CH2:30][C:31]([O:33]C(C)(C)C)=[O:32])[C:5]2=[CH:6][CH:7]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([CH2:15][C:16]4[C:17]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)=[N:18][O:19][C:20]=4[CH3:21])[C:11]3=[O:28])[C:9](=[O:29])[N:8]([CH2:30][C:31]([OH:33])=[O:32])[C:5]2=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 24827318tert-butyl [5-chloro-1'-[(5-methyl-3-phenylisoxazol-4-yl)methyl]-2,2'-dioxospiro[indole-3,3'-pyrrolidin]-1(2H)-yl]acetate

Product 1

HCID 24776299[5-chloro-1'-[(5-methyl-3-phenylisoxazol-4-yl)methyl]-2,2'-dioxospiro[indole-3,3'-pyrrolidin]-1(2H)-yl]acetic acidYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An ice-cold solution of tert-butyl [5-chloro-1′-[(5-methyl-3-phenylisoxazol-4-yl)methyl]-2,2′-dioxospiro[indole-3,3′-pyrrolidin]-1(2H)-yl]acetate, intermediate 42 (80.00 mg; 0.15 mmol) in DCM (8.00 ml) was treated with trifluoroacetic acid (2.00 ml). After stirring at room temperature for 5 h, the solvents were removed in vacuo. Toluene was added twice and removed in vacuo to give the titla compound as a white solid in 91% yield (96.3% purity by HPLC). MS (ESI+): 466.3; MS (ESI−): 464.4

Workup

  1. customthe solvents were removed in vacuo
  2. additionToluene was added twice
  3. customremoved in vacuo

Sources & evidence

ORD record
ord-001d21c3cfdf48d7b74f64f059e88d20
Source dataset
uspto-grants-2012_08
Patent number
US08236963B2

Reaction notes

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