Trifluoroacetic acid water → HCID 135423412, compound

HRID 1784128Notes

Reaction equation

HRID 1784128 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]3[NH:16][C:15]([C:17]([C:53]4[C:58]([CH3:59])=[CH:57][C:56]([CH3:60])=[CH:55][C:54]=4[CH3:61])=[C:18]4[N:52]=[C:21]([C:22]([C:42]5[CH:47]=[CH:46][C:45]([C:48]([CH3:51])([CH3:50])[CH3:49])=[CH:44][CH:43]=5)=[C:23]5[NH:41][C:26](=[C:27]([CH:33]6OCC(C)(C)C[O:34]6)[C:28]6[CH:29]=[CH:30][C:31]=2[N:32]=6)[CH:25]=[CH:24]5)[CH:20]=[CH:19]4)=[CH:14][CH:13]=3)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O.O>C(Cl)Cl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:12]3[NH:16][C:15]([C:17]([C:53]4[C:54]([CH3:61])=[CH:55][C:56]([CH3:60])=[CH:57][C:58]=4[CH3:59])=[C:18]4[N:52]=[C:21]([C:22]([C:42]5[CH:47]=[CH:46][C:45]([C:48]([CH3:51])([CH3:50])[CH3:49])=[CH:44][CH:43]=5)=[C:23]5[NH:41][C:26](=[C:27]([CH:33]=[O:34])[C:28]6[CH:29]=[CH:30][C:31]=2[N:32]=6)[CH:25]=[CH:24]5)[CH:20]=[CH:19]4)=[CH:14][CH:13]=3)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 22392675Trifluoroacetic acid waterHCID 135481084HCID 135481084, compound

Product 1

HCID 135423412HCID 135423412, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Following a general procedure,22 a solution of 4 (43 mg, 0.05 mmol) in CH2Cl2 (5 mL) was treated with TFA/water (0.5 mL, 1:1) to give a biphasic solution. After stirring at room temperature for 2.5 h, CH2Cl2 was added. The organic layer was washed (saturated aqueous NaHCO3 and brine), dried (Na2SO4), concentrated, and chromatographed (silica, CH2Cl2/hexanes) to give a purple solid (34.8 mg, 92%): IR (neat) 1674, 1557, 1110 cm−1; 1H NMR δ −1.90 (s, 2H), 1.61 (s, 18H), 1.84 (s, 6H), 2.61 (s, 3H), 7.26 (s, 2H), 7.75-7.78 (m, 4H), 8.08-8.11 (m, 4H), 8.59 (d, J=4.4 Hz, 2H), 8.69 (d, J=4.4 Hz, 2H), 9.01 (d, J=5.2 Hz, 2H), 10.03 (br s, 2H), 12.50 (s, 1H); 13C NMR δ 195.1, 151.2, 139.2, 138.7, 138.3, 137.7, 134.2, 128.0, 124.4, 124.0, 122.6, 107.7, 35.2, 31.9, 29.9, 21.8, 21.7; LD-MS obsd 721.86; FAB-MS obsd 721.3931, calcd 720.3828 (C50H48N4O); λabs 428, 528, 567, 600, 657 nm.

Workup

  1. customto give a biphasic solution
  2. washThe organic layer was washed (saturated aqueous NaHCO3 and brine)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customchromatographed (silica, CH2Cl2/hexanes)

Sources & evidence

ORD record
ord-1ab555f16b654ade937dccaeb6cb5b60
Source dataset
uspto-grants-2009_03
Patent number
US07501507B2

Reaction notes

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