Trifluoroacetic acid → HCID 11227839, compound

HRID 1174393Notes

Reaction equation

HRID 1174393 reaction equation
[CH2:1]([C@H:8]([NH:39][C:40](=[O:70])[C@H:41]([CH2:47][C:48]([NH:50]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:49])[NH:42][C:43]([O:45][CH3:46])=[O:44])[C@@H:9]([OH:38])[CH2:10][C@@H:11]([NH:25][C:26](=[O:37])[C@H:27]([C:33]([CH3:36])([CH3:35])[CH3:34])[NH:28][C:29]([O:31][CH3:32])=[O:30])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:46][O:45][C:43](=[O:44])[NH:42][C@@H:41]([CH2:47][C:48]([NH2:50])=[O:49])[C:40](=[O:70])[NH:39][C@@H:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@@H:9]([OH:38])[CH2:10][C@H:11]([CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:17][CH:18]=1)[NH:25][C:26](=[O:37])[C@H:27]([C:33]([CH3:36])([CH3:35])[CH3:34])[NH:28][C:29](=[O:30])[O:31][CH3:32]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131728540HCID 131728540, compound

Product 1

HCID 11227839HCID 11227839, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 168C (27.7 mg, 0.027 mmol) in dichloromethane (0.5 mL) was treated with trifluoroacetic acid (0.25 mL) at 25° C. for 2 h. The solvents were evaporated, and the residue was dissolved in dichloromethane, washed with saturated sodium bicarbonate, dried over MgSO4, filtered, and the solvents were evaporated. The crude residue was purified by silica gel chromatography eluting with a gradient of dichloromethane, 100% ethyl acetate, and 95% ethyl acetate/7% methanol to give the title compound (4 mg, 16%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.81(s, 9H), 1.53(m, 2H), 2.42-2.30(m, 2H), 2.64-2.60(m, 1H), 2.79-2.71(m, 4H), 3.50(s, 3H), 3.54(s, 3H), 3.61(m, 1H), 3.79(d, J=4.04 Hz, 1H), 4.03(m, 4.13(m, 1H), 4.27(m, 1H), 4.57(bs, 1H), 6.17(m, 1H), 6.84(m, 1H), 7.12(m, 1H), 7.21-7.19(m, 7H), 7.27(m, 1H), 7.48(d, J=7.81 Hz, 1H), 7.82(bs, 2H), 7.87-7.86(d, J=7.81 Hz, 2H), 8.62-8.61(d, J=4.39 Hz, 1H).

Workup

  1. customThe solvents were evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with saturated sodium bicarbonate
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were evaporated
  7. customThe crude residue was purified by silica gel chromatography
  8. washeluting with a gradient of dichloromethane, 100% ethyl acetate, and 95% ethyl acetate/7% methanol

Sources & evidence

ORD record
ord-4472444685c8424394f4204de5a97778
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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