Triethylamine → HCID 86687109, compound

HRID 1402261Notes

Reaction equation

HRID 1402261 reaction equation
[C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])(=[O:4])[CH:2]=[CH2:3].Cl.[CH2:11]([O:18][C:19](=[O:25])[C@@H:20]1[CH2:24][CH2:23][CH2:22][NH:21]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCN(CC)CC>C(O)(C)(C)C>[CH2:11]([O:18][C:19]([C@@H:20]1[CH2:24][CH2:23][CH2:22][N:21]1[CH2:3][CH2:2][C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])=[O:25])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15458tert-Butyl acrylateHCID 2733413Proline benzyl ester hydrochloride

Product 1

HCID 86687109HCID 86687109, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
80 °C

Procedure

Tert-butyl acrylate (5.00 mL) was added to a solution of L-proline benzyl ester hydrochloride salt (1.10 g, 4.54 mmol) and Et3N (632 μL, 4.54 mmol) in tert-butanol (5.00 mL). The reaction was heated to 80° C. for 3 h then and evaporated in vacuo. The residue was purified by FCC, using 0-50% EtOAc in cyclohexane, to give the title compound (1.20 g, 79%). 1H NMR (300 MHz, CDCl3): 1.43 (9H, s), 1.72-2.00 (3H, m), 2.08 (1H, m), 2.39-2.48 (3H, m), 2.72 (1H, ddd, J 12.2, 8.4, 6.7), 3.00 (1H, dt, J 12.3, 7.8), 3.13 (1H, m), 3.28 (1H, dd, J 8.6, 5.4), 5.13 (1H, d, J 12.3), 5.18 (1H, d, J 12.3), 7.29-7.39 (5H, m).

Workup

  1. customevaporated in vacuo
  2. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-1781e57863244d74a31b6b191d964bb9
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

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