Trifluoroacetic acid → HCID 58236615, compound

HRID 409988Notes

Reaction equation

HRID 409988 reaction equation
[F:1][C:2]1[CH:42]=[C:41]([NH:43][C:44]([NH:46][C:47]2[CH:51]=[C:50]([CH3:52])[O:49][N:48]=2)=[O:45])[CH:40]=[CH:39][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:38]=[CH:37][C:17]([CH2:18][N:19]([CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH3:36])C(=O)OC(C)(C)C)=[CH:16][CH:15]=3)[S:13][C:6]=12.FC(F)(F)C(O)=O>ClCCl>[CH2:18]([C:17]1[CH:37]=[CH:38][C:14]([C:12]2[S:13][C:6]3[C:7](=[N:8][CH:9]=[CH:10][C:5]=3[O:4][C:3]3[CH:39]=[CH:40][C:41]([NH:43][C:44]([NH:46][C:47]4[CH:51]=[C:50]([CH3:52])[O:49][N:48]=4)=[O:45])=[CH:42][C:2]=3[F:1])[CH:11]=2)=[CH:15][CH:16]=1)[NH:19][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH3:36]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58236575HCID 58236575, compound

Product 1

HCID 58236615HCID 58236615, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 367 (0.074 g, 0.10 mmol) in dichloromethane (50 mL) was added trifluoroacetic acid (1.0 mL). The reaction mixture was stirred for 3 h at r.t. then concentrated and the residue was partitioned between dichloromethane and sat. NaHCO3. The organic phase was collected, washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by Gilson reverse phase HPLC (35-75% MeOH/H2O, Aquasil C18, 30 min) and lyophilized. The purified product (containing some formic acid from the HPLC) was partitioned between dichloromethane and 1M NaOH). The organic phase was collected, dried (MgSO4), filtered and concentrated to give compound 368 (0.033 g, 0.052 mmol, 52% yield).

Workup

  1. concentrationthen concentrated
  2. customthe residue was partitioned between dichloromethane and sat. NaHCO3
  3. customThe organic phase was collected
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by Gilson reverse phase HPLC (35-75% MeOH/H2O, Aquasil C18, 30 min)
  9. additionThe purified product (containing some formic acid from the HPLC)
  10. customwas partitioned between dichloromethane and 1M NaOH)
  11. customThe organic phase was collected
  12. dry with materialdried (MgSO4)
  13. filtrationfiltered
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-47d2bdff37b547e989bf79865f08567c
Source dataset
uspto-grants-2014_06
Patent number
US08759522B2

Reaction notes

Loading…