Trifluoroacetic acid → HCID 22730844, compound

HRID 2085747Notes

Reaction equation

HRID 2085747 reaction equation
[O:1]1CCCO[CH:2]1[CH2:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:45]=[CH:44][C:18]([C:19]([NH:21][S:22]([C:25]3[CH:30]=[CH:29][C:28]([NH:31][CH2:32][CH2:33][S:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[C:27]([N+:41]([O-:43])=[O:42])[CH:26]=3)(=[O:24])=[O:23])=[O:20])=[CH:17][CH:16]=2)[CH2:11][CH2:10]1.C(O)(C(F)(F)F)=O>ClCCl.O>[N+:41]([C:27]1[CH:26]=[C:25]([S:22]([NH:21][C:19](=[O:20])[C:18]2[CH:44]=[CH:45][C:15]([N:12]3[CH2:11][CH2:10][CH:9]([CH2:8][CH2:7][CH:2]=[O:1])[CH2:14][CH2:13]3)=[CH:16][CH:17]=2)(=[O:24])=[O:23])[CH:30]=[CH:29][C:28]=1[NH:31][CH2:32][CH2:33][S:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)([O-:43])=[O:42]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22730351HCID 22730351, compound

Product 1

HCID 22730844HCID 22730844, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of Example 203C (250 mg, 0.4 mmol), in dichloromethane (5 mL), TFA (1.5 mL), and 1 drop water was stirred at room temperature for 48 hours. The reaction mixture was diluted with dichloromethane, washed sequentially with water, saturated NaHCO3, and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with dichloromethane 0.5-1.0% methanol to provide the desired product. MS (APCI) m/e 597 (M+H)+; 1H NMR (300 MHz, CDCl3) δ9.80 (s, 1H), 8.87 (d, 1H), 8.67 (t, 1H), 8.47 (s, 1H), 8.15 (dd, 1H), 7.63 (d, 2H), 7.40 (m, 2H), 7.24-7.34 (m, 4H), 6.87 (d, 2H), 6.82 (m, 2H), 3.87 (d, 2H), 3.58 (m, 4H), 3.21 (t, 2H), 2.86 (m, 2H), 2.50 (m, 2H), 1.80 (m, 2H), 1.62 (m, 2H), 1.55 (s, 4H) 1.31 (m, 2H).

Workup

  1. washwashed sequentially with water, saturated NaHCO3, and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash column chromatography on silica gel with dichloromethane 0.5-1.0% methanol

Sources & evidence

ORD record
ord-363b4d1979d04d3ea3660dd7476de9d0
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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