Triethylamine → HCID 69241548, compound

HRID 1394142Notes

Reaction equation

HRID 1394142 reaction equation
[C:1]([O:5][C:6]([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][CH2:19][CH2:18]1)=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:22]1([C:28](Cl)=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C(N(CC)CC)C>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][NH:14][C:28]([CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[O:29])[CH2:10][C@H:9]1[C:15]([N:17]1[CH2:18][CH2:19][CH2:20][CH2:21]1)=[O:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 59681845HCID 59681845, compound

Product 1

HCID 69241548HCID 69241548, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (2S, 4R)-4-aminomethyl-2-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylic acid tert-butyl ester (0.15 g, 0.51 mmol, Example 39C) in dichloromethane (2 mL) at room temperature was added cyclohexanecarbonyl chloride (0.092 g, 0.65 mmol) and triethylamine (0.10 mL, 0.75 mmol). The mixture was stirred at room temperature for 12 hours, concentrated under reduced pressure and the residue taken up in water and extracted with ethyl acetate (2×). The combined ethyl acetate layers were washed consecutively with saturated aqueous NaHCO3, 10% KHSO4 (aq), brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography with 30-40% ethyl acetate:hexane to provide the title compound. MS (CI) m/z 408 (M+1)+; 1H NMR (300 MHz, CDCl3) δ ppm 4.40-4.28 (m, 1H), 3.88-3.66 (m, 2H), 3.56-3.25 (m, 4H), 3.22-3.16 (m, 2H), 2.57 (m, 2H), 2.55 (m, 1H), 1.99-1.61, (m, 13H), 1.41 (m, 9H), 1.51 (m, 2H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionextracted with ethyl acetate (2×)
  3. washThe combined ethyl acetate layers were washed consecutively with saturated aqueous NaHCO3, 10% KHSO4 (aq), brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography with 30-40% ethyl acetate

Sources & evidence

ORD record
ord-c8138a2fdf5a4dd69d8488b9ca569481
Source dataset
uspto-grants-2008_03
Patent number
US07348346B2

Reaction notes

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