Trifluoroacetic acid → HCID 131723510, compound

HRID 393478Notes

Reaction equation

HRID 393478 reaction equation
[CH3:1][O:2][C:3](=[O:33])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:28](=[O:29])[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([C:30]#[N:31])[CH:26]=3)[C:21]2=[O:32])=[CH:16][CH:15]=1)[NH:5]C(OC(C)(C)C)=O.[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37]>ClCCl>[OH:38][C:36]([C:35]([F:40])([F:39])[F:34])=[O:37].[CH3:1][O:2][C:3](=[O:33])[C@H:4]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([N:20]2[C:28](=[O:29])[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([C:30]#[N:31])[CH:26]=3)[C:21]2=[O:32])=[CH:18][CH:19]=1)[NH2:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54317643HCID 54317643, compound

Product 1

HCID 131723510HCID 131723510, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(5-cyano-1,3-dioxo-2H-isoindol-2-yl)-N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine methyl ester (1.33 mmol, 0.6 g) in dichloromethane (12 mL) was added trifluoroacetic acid (3 mL) at room temperature. The reaction mixture was stirred for 15 h at room temperature at which time TLC analysis of the mixture indicated the absence of starting material. The solvent was removed under vacuum and the residue was azeotrophed with toluene (2×10 mL) and dried under high vacuum to afford 0.46 g (100%) of a yellow solid. HR MS (C19H15N3O4): Obs mass, 350.0156. Calcd mass, 350.0183 (M+H).

Workup

  1. customThe solvent was removed under vacuum
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-4248ca0684b74caa8dddcf932f5e9c23
Source dataset
uspto-grants-2004_10
Patent number
US06806365B2

Reaction notes

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