Trifluoroacetic acid → HCID 10791078, compound

HRID 1384451Notes

Reaction equation

HRID 1384451 reaction equation
C([O:5][C:6](=[O:46])[C@@H:7]([NH:38]C(OC(C)(C)C)=O)[CH2:8][CH2:9][CH2:10][CH2:11][N:12]([C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])(C)(C)C.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(Cl)Cl>[NH2:38][C@@H:7]([CH2:8][CH2:9][CH2:10][CH2:11][N:12]([C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:19])[C:6]([OH:46])=[O:5]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 10817910HCID 10817910, compound

Product 1

HCID 10791078HCID 10791078, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under argon, 8 (271 mg, 0.422 mmol) was added to a mixture of trifluoroacetic acid (770 mg, 6.7 mmol), CH2Cl2 (3.0 mL), and triethylsilane (330 mg, 2.8 mmol); this was stirred at room temperature for 23 hours. The reaction mixture was concentrated; the resultant oil was dissolved in water (5.0 mL) and adjusted to pH 7 with saturated NaHCO3 solution. This solution was then concentrated; the residue was purified by chromatography on a C-18 column (30% acetone/water, followed by 55% acetone/water) to give 9 (137 mg, 67%) as a colorless oil: 1H NMR (19.7° C.) δ1.30-1.66 (m, 8 H), 1.78 (m, 2 H), 3.09 (m, 2 H), 3.20-3.33 (m, 4 H), 3.45 (m, 1 H), 5.05(s, 2H), 5.09 (s, 2 H), 7.26-7.37 (m, 10 H); HRMS m/z calcd for C26H36N3O6 486.2604, found 486.2614.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe resultant oil was dissolved in water (5.0 mL)
  3. concentrationThis solution was then concentrated
  4. customthe residue was purified by chromatography on a C-18 column (30% acetone/water, followed by 55% acetone/water)

Sources & evidence

ORD record
ord-257ed093a519446fa44371a67b2c7f84
Source dataset
uspto-grants-2001_07
Patent number
US06258931B1

Reaction notes

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