Trifluoroacetic acid → 5-[(Morpholin-4-yl)carbonyl]isoindoline trifluoroacetate

HRID 268717Notes

Reaction equation

HRID 268717 reaction equation
C(OC([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[O:18])[CH:14]=2)[CH2:9]1)=O)(C)(C)C.[C:25]([OH:31])([C:27]([F:30])([F:29])[F:28])=[O:26]>C(Cl)Cl>[F:28][C:27]([F:30])([F:29])[C:25]([OH:31])=[O:26].[N:19]1([C:17]([C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[CH2:9][NH:8][CH2:16]3)=[O:18])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 17986287N-t-Butoxycarbonyl-5-[(morpholin-4-yl)carbonyl]isoindoline

Product 1

HCID 179862825-[(Morpholin-4-yl)carbonyl]isoindoline trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-t-butoxycarbonyl-5-[(morpholin-4-yl)carbonyl] isoindoline (D19) (300 mg) in DCM (5 ml) at rt was treated with TFA (2 ml) for 1 h and then evaporated. The residue was re-evaporated from DCM/toluene to give the title compound (D20) (305 mg). MS electrospray (+ion) 233 (MH+). 1H NMR δ (CDCl3): 10.10 (1H, m), 7.25 (3H, m), 4.64 (2H, m), 4.53 (2H, m), 3.54 (8H, m).

Workup

  1. customevaporated
  2. customThe residue was re-evaporated from DCM/toluene

Sources & evidence

ORD record
ord-64cc4dae406c49ce9586dbe1801e99bf
Source dataset
uspto-grants-2008_11
Patent number
US07446103B2

Reaction notes

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