Trifluoroacetic acid → HCID 53491470, compound

HRID 1400857Notes

Reaction equation

HRID 1400857 reaction equation
[F:1][C:2]1[CH:37]=[C:36]([NH:38][C:39]([NH:41][C:42]2[CH:46]=[C:45]([CH3:47])[O:44][N:43]=2)=[O:40])[CH:35]=[CH:34][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:19]=[CH:18][C:17]([CH2:20][CH2:21][N:22]([CH2:30][CH2:31][O:32][CH3:33])C(=O)OC(C)(C)C)=[CH:16][CH:15]=3)[S:13][C:6]=12.C(O)(C(F)(F)F)=O>ClCCl>[F:1][C:2]1[CH:37]=[C:36]([NH:38][C:39]([NH:41][C:42]2[CH:46]=[C:45]([CH3:47])[O:44][N:43]=2)=[O:40])[CH:35]=[CH:34][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:15]=[CH:16][C:17]([CH2:20][CH2:21][NH:22][CH2:30][CH2:31][O:32][CH3:33])=[CH:18][N:19]=3)[S:13][C:6]=12

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67442432HCID 67442432, compound

Product 1

HCID 53491470HCID 53491470, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 182 (0.17 g, 0.26 mmol) was suspended in dichloromethane (50 mL) and TFA (1 mL) was added. This solution was stirred for 1 h then the mixture was concentrated. The residue was partitioned between ethyl acetate and water, washed with 3M NaOH and brine, then dried over anhydrous MgSO4, filtered and concentrated. The residue was triturated with diethyl ether and dried in vacuo to afford title compound 183 (0.125 g, 87% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.74 (s, 1H); 9.33 (s, 1H); 8.52 (d, J=5.5, 1H): 8.51-8.50 (m, 1H); 8.29 (s, 1H); 8.18 (d, J=8.0, 1H): 7.81 (dd, J=8.2, 2.2, 1H); 7.74 (J=12.9, 2.5, 1H); 7.46 (t. J=9.0, 1H); 7.30-7.27 (m, 1H); 6.66 (d, J=5.5, 1H); 6.55 (s, 1H); 3.37 (t, J=5.7, 2H); 3.22 (s, 1H); 2.82-2.75 (m, 4H); 2.68 (t, J=5.5, 2H); 2.37 (s, 3H). LRMS (M+H): 563.5.

Workup

  1. concentrationthe mixture was concentrated
  2. customThe residue was partitioned between ethyl acetate and water
  3. washwashed with 3M NaOH and brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was triturated with diethyl ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-7ab32738fb5a4b71b07ff727b91c7e89
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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