Trifluoroacetic acid → HCID 22337004, compound

HRID 585504Notes

Reaction equation

HRID 585504 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[C:19](=[O:20])[CH:18]3[CH:13]([CH2:14][CH:15]=[CH:16][CH:17]3[NH:21]C(=O)OC(C)(C)C)[C:12]2=[O:29])=[CH:5][CH:4]=1)#[N:2].FC(F)(F)C(O)=O>ClCCl>[NH2:21][CH:17]1[CH:16]=[CH:15][CH2:14][CH:13]2[CH:18]1[C:19](=[O:20])[N:11]([CH2:10][CH2:9][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=1)[C:12]2=[O:29]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20824220HCID 20824220, compound

Product 1

HCID 22337004HCID 22337004, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.008 g (2.55 mmol) of tert-butyl 2-[2-(4-cyanophenyl)ethyl]-1,3-dioxo-2,3,3a,4,7,7a-hexahydro-1H-isoindol-4-ylcarbamate are dissolved in 20 ml of dichloromethane, and 0.79 ml (10.2 mmol) of trifluoroacetic acid is added. After 4 h of stirring at room temperature, the reaction mixture is concentrated using a rotary evaporator and worked up using EtOAc and saturated aqueous NaHCO3 solution. The organic phase is dried over magnesium sulfate, filtered and concentrated using a rotary evaporator. The crude product is chromatographed on silica gel (CH2Cl2/EtOH=50/1+0.5% aqueous NH3 solution (25% strength)). This gives 530 mg (70% of theory) of the desired compound. MS=337 (M+H+MeCN), 296 (M+H), rt (Method 4)=2.04 min.

Workup

  1. concentrationthe reaction mixture is concentrated
  2. customa rotary evaporator
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customa rotary evaporator
  7. customThe crude product is chromatographed on silica gel (CH2Cl2/EtOH=50/1+0.5% aqueous NH3 solution (25% strength))
  8. customMS=337 (M+H+MeCN), 296 (M+H), rt (Method 4)=2.04 min.

Sources & evidence

ORD record
ord-cfd084a99a35436eadae197b74138a7c
Source dataset
uspto-grants-2005_08
Patent number
US06933295B2

Reaction notes

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