Triethylamine → HCID 68862178, compound

HRID 1726007Notes

Reaction equation

HRID 1726007 reaction equation
[NH2:1][CH2:2][CH2:3][C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].C(N([CH2:21][CH3:22])CC)C>ClCCl>[CH2:12]([O:11][C:9]([NH:1][CH2:2][CH2:3][C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:10])[C:22]1[CH:21]=[CH:8][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 7016511tert-Butyl (2S)-2-(2-aminoethyl)pyrrolidine-1-carboxylate

Product 1

HCID 68862178HCID 68862178, compoundYield 177.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of Example 535B (560 mg, 2.62 mmol), benzyloxycarbonylsuccinimide ester (0.783 g, 3.93 mmol, and triethylamine (0.55 mL, 3.93 mmol) in 10 mL of dichloromethane was stirred overnight, concentrated, treated with ethyl acetate, washed with brine, 10% potassium hydrogen sulfate (3×), and brine (3×), dried (MgSO4), filtered, concentrated, and purified by silica gel column chromatography, eluting with 20% ethyl acetate in n-hexane to provide 0.81 g of the desired product. MS (ESI(+)) m/e 347 (M+H)+; 1H NMR (300 MHz, CDCl3) δ 7.28-7.39 (m, 5H), 7.23 (br, 1H), 5.00 (s, 2H), 3.62-3.74 (m, 1H), 3.19-3.29 (m, 2H), 2.92-3.05 (m, 2H), 1.73-1.91 (m, 5H), 1.54-1.62 (m, 1H), 1.38 (s, 9H).

Workup

  1. concentrationconcentrated
  2. additiontreated with ethyl acetate
  3. washwashed with brine, 10% potassium hydrogen sulfate (3×), and brine (3×)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography
  8. washeluting with 20% ethyl acetate in n-hexane

Sources & evidence

ORD record
ord-21503d547eeb4c65984d6100e9b5450b
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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