Sodium hydride → HCID 15288189, compound

HRID 267086Notes

Reaction equation

HRID 267086 reaction equation
[CH3:1][O:2][C:3](=[O:10])[C@@H:4]1[CH2:8][CH2:7][C:6](=[O:9])[NH:5]1.[H-].[Na+].[N+:13]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Br)=[CH:18][CH:17]=1)([O-:15])=[O:14]>C1COCC1>[CH3:1][O:2][C:3](=[O:10])[C@@H:4]1[CH2:8][CH2:7][C:6](=[O:9])[N:5]1[CH2:20][C:19]1[CH:22]=[CH:23][C:16]([N+:13]([O-:15])=[O:14])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 660114-Nitrobenzyl bromideHCID 78646Methyl 5-oxo-L-prolinate

Product 1

HCID 15288189HCID 15288189, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-Pyroglutamic acid methyl ester (0.200 g, 1.40 mmol) was dissolved in dry THF (5 ml) and NaH (0.061 g, 1.5 mmol) was added. After gas evolution ceased, 4-nitrobenzyl bromide (0.332 g, 1.54 mmol) was added and the mixture stirred for 1 h. The reaction was quenched with saturated NaHCO3 solution (40 mL) and extracted with EtOAc (2×50 ml). The organic layers were washed with water, brine, dried (MgSO4), filtered, and concentrated to give the title compound as a solid. 1H NMR (CDCl3) δ 8.19 (d, 2H, J=8.6 Hz), 7.40 (d, 2H, J=8.6 Hz), 5.29 (d, 1H, J=15 Hz), 4.19 (d, 1H, J=15 Hz), 4.02 (dd, 1H, J=3,9 Hz), 3.79 (s, 3H), 2.54-2.67 (m, 1H), 2.42-2.51 (m, 1H), 2.27-2.39 (m, 1H), 2.11-2.21 (m, 1H).

Workup

  1. customThe reaction was quenched with saturated NaHCO3 solution (40 mL)
  2. extractionextracted with EtOAc (2×50 ml)
  3. washThe organic layers were washed with water, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-20837e01a95048b59f7889222de3bf4e
Source dataset
uspto-grants-1997_07
Patent number
US05652257

Reaction notes

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