Trifluoroacetic acid → HCID 22086854, compound

HRID 2227371Notes

Reaction equation

HRID 2227371 reaction equation
C([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]=[C:17]3[N:22]([CH2:23][C:24]4[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:25]=4[F:31])[C:21]([CH3:32])=[C:20]([CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:19](=[O:40])[N:18]3[C:41]=2[CH2:42][N:43]([CH3:51])[CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[CH:11][CH:10]=1)(OC(C)(C)C)=O.FC(F)(F)C(O)=O>ClCCl>[F:30][C:29]1[CH:28]=[CH:27][CH:26]=[C:25]([F:31])[C:24]=1[CH2:23][N:22]1[C:21]([CH3:32])=[C:20]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:19](=[O:40])[N:18]2[C:41]([CH2:42][N:43]([CH3:51])[CH2:44][C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)=[C:15]([C:12]3[CH:13]=[CH:14][C:9]([NH2:8])=[CH:10][CH:11]=3)[N:16]=[C:17]12

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 22281802HCID 22281802, compound

Product 1

HCID 22086854HCID 22086854, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound obtained in Example 19 (0.53 g, 0.77 mol) in dichloromethane (20 ml) is added trifluoroacetic acid (0.24 ml, 3.07 mmol) with ice-cooling. An additional amount of trifluoroacetic acid (1.5 ml) is added at room temperature and is stirred for 5 hours at room temperature. The reaction mixture is partitioned between chloroform (100 ml) and aqueous saturated NaHCO3 solution (30 ml). The aqueous layer is extracted with chloroform (30 ml). The combined organic solution is washed with saturated saline (20 ml), dried over Na2SO4, successively evaporated under reduced pressure to give the residue, which is chromatographed on silica gel to afford a pale brown colorless amorphous (0.41 g, 90%).

Workup

  1. temperaturecooling
  2. customThe reaction mixture is partitioned between chloroform (100 ml) and aqueous saturated NaHCO3 solution (30 ml)
  3. extractionThe aqueous layer is extracted with chloroform (30 ml)
  4. washThe combined organic solution is washed with saturated saline (20 ml)
  5. dry with materialdried over Na2SO4
  6. customsuccessively evaporated under reduced pressure
  7. customto give the residue, which
  8. customis chromatographed on silica gel
  9. customto afford a pale brown colorless amorphous (0.41 g, 90%)

Sources & evidence

ORD record
ord-46875cc7dba84fd28591243e3df8c28d
Source dataset
uspto-grants-2002_07
Patent number
US06413972B1

Reaction notes

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