Trifluoroacetic acid → HCID 11631242, compound

HRID 2242185Notes

Reaction equation

HRID 2242185 reaction equation
C(OC([N:8]1[CH2:12][C@@H:11]([CH2:13][NH2:14])[CH2:10][C@H:9]1[C:15]([N:17]1[CH2:21][CH2:20][S:19][CH2:18]1)=[O:16])=O)(C)(C)C.[CH2:22](N(CC)CC)C.[N:29]1([C:34](Cl)=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30]1.FC(F)(F)C(O)=O>ClCCl>[CH:33]1([NH:29][C:34]([NH:14][CH2:13][C@H:11]2[CH2:10][C@@H:9]([C:15]([N:17]3[CH2:21][CH2:20][S:19][CH2:18]3)=[O:16])[NH:8][CH2:12]2)=[O:35])[CH2:32][CH2:31][CH2:30][CH2:22]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 709371-Pyrrolidinecarbonyl chlorideHCID 69241294HCID 69241294, compound

Product 1

HCID 11631242HCID 11631242, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a mixture of Example 17D (32.0 mg, 0.1 mmol) and triethylamine (0.03 mL, 0.2 mmol) in anhydrous dichloromethane (2 mL) was added pyrrolidine-1-carbonyl chloride (16.0 mg, 0.12 mmol) and the mixture was allowed to stir for 6 hours at room temperature. The mixture was concentrated under reduced pressure and the residue was chromatographed on a Biotage 40M eluting with 20% hexane/80% ethyl acetate to provide a yellow oil. The oil was dissolved in anhydrous dichloromethane (5 mL) and trifluoroacetic acid (0.075 mL) in dichloromethane (0.075 mL) were added to the mixture via syringe. The mixture was allowed to stir for 5 hours at room temperature and concentrated under reduced pressure to provide the titled compound. MS (ESI) m/e 313 (M+H)+; 1H NMR (400 MHz, CD3OD) δ ppm 1.72 (m, 1 H) 1.91 (t, 4 H) 2.66 (m, 2 H) 3.08 (m, 1 H) 3.16 (m, 2 H) 3.26 (m, 2 H) 3.30 (t, 4 H) 3.45 (m, 1 H) 3.74 (m, 1 H) 3.87 (m, 1 H) 4.51 (m, 1 H) 4.62 (m, 2 H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was chromatographed on a Biotage 40M
  3. washeluting with 20% hexane/80% ethyl acetate
  4. customto provide a yellow oil
  5. stirringto stir for 5 hours at room temperature
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bff6a31eb9034bc4a016bbb1f2fc6c8b
Source dataset
uspto-grants-2010_03
Patent number
US07671076B2

Reaction notes

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