Trifluoroacetic acid → HCID 131736631, compound

HRID 1481305Notes

Reaction equation

HRID 1481305 reaction equation
[Cl:1][C:2]1[N:3]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])[C:4]2[C@@H:5]([NH:27]C(=O)OC(C)(C)C)[CH2:6][CH2:7][CH2:8][C@@H:9]([CH3:26])[C:10](=[O:25])[NH:11][C:12]3[C:17]([C:18]=1[N:19]=2)=[CH:16][CH:15]=[C:14]([NH:20][C:21]([O:23][CH3:24])=[O:22])[CH:13]=3.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:27][C@@H:5]1[C:4]2=[N:19][C:18](=[C:2]([Cl:1])[N:3]2[CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:41])([CH3:42])[CH3:40])[C:17]2[C:12](=[CH:13][C:14]([NH:20][C:21](=[O:22])[O:23][CH3:24])=[CH:15][CH:16]=2)[NH:11][C:10](=[O:25])[C@H:9]([CH3:26])[CH2:8][CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131736632HCID 131736632, compound

Product 1

HCID 131736631HCID 131736631, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

135I (0.476 g, 0.765 mmol) was treated with TFA (2.95 mL, 38.2 mmol) in DCM (15 mL). After 1 hour, the reaction mixture was concentrated to dryness. The residue was dissolved in EtOAc and washed with 1.5M potassium phosphate. The organic layer was washed further with brine, dried over sodium sulfate, filtered, and concentrated. This material was carried forward as is. MS (ESI) m/z: 522.3 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated to dryness
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with 1.5M potassium phosphate
  4. washThe organic layer was washed further with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-cffccc4c81584e519a793d5510e598b3
Source dataset
uspto-grants-2016_08
Patent number
US09409908B2

Reaction notes

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