Trifluoroacetic acid → HCID 24768828, compound

HRID 502529Notes

Reaction equation

HRID 502529 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]([O:15][CH2:16][O:17][C:18](=[O:46])[N:19]([C:43](=[O:45])[CH3:44])[CH2:20][C@@H:21]1[O:25][C:24](=[O:26])[N:23]([C:27]2[CH:32]=[CH:31][C:30]([N:33]3[CH2:40][C:39]4[C:35](=[N:36][N:37]([CH3:41])[CH:38]=4)[CH2:34]3)=[C:29]([F:42])[CH:28]=2)[CH2:22]1)=[O:14])=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[C:43]([N:19]([CH2:20][C@@H:21]1[O:25][C:24](=[O:26])[N:23]([C:27]2[CH:32]=[CH:31][C:30]([N:33]3[CH2:40][C:39]4[C:35](=[N:36][N:37]([CH3:41])[CH:38]=4)[CH2:34]3)=[C:29]([F:42])[CH:28]=2)[CH2:22]1)[C:18]([O:17][CH2:16][O:15][C:13]([C@@H:9]1[CH2:10][CH2:11][CH2:12][NH:8]1)=[O:14])=[O:46])(=[O:45])[CH3:44]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59427270HCID 59427270, compound

Product 1

HCID 24768828HCID 24768828, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 11 (1 equiv) in dichloromethane at rt under nitrogen is added TFA (5 equiv) dropwise. The reaction mixture is stirred at rt for 2 h, concentrated in vacuo, purified directly by HPLC (C-18 column, 0-100% gradient elution, MeCN:H2O with 0.1% TFA), and fractions containing product are lyophilized to give the title compound. Theoretical MS 545 (M+1)+

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified directly by HPLC (C-18 column, 0-100% gradient elution, MeCN:H2O with 0.1% TFA), and fractions
  3. additioncontaining product

Sources & evidence

ORD record
ord-a2639935d5f04829a25cde8a4ed8bad7
Source dataset
uspto-grants-2010_08
Patent number
US07776855B2

Reaction notes

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