Sodium Carbonate → HCID 71547324, compound

HRID 240415Notes

Reaction equation

HRID 240415 reaction equation
[NH2:1][C@@H:2]1[CH2:17][N:5]2[CH2:6][CH2:7][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:9][C@@H:4]2[CH2:3]1.C(=O)([O-])[O-].[Na+].[Na+].[F:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1>ClCCl>[F:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([NH:1][C@@H:2]2[CH2:17][N:5]3[CH2:6][CH2:7][N:8]([C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[CH2:9][C@@H:4]3[CH2:3]2)=[O:30])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 678794-Fluorobenzoyl chlorideHCID 43810901HCID 43810901, compound

Product 1

HCID 71547324HCID 71547324, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (7S,8aS)-tert-butyl 7-aminohexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate (0.241 g, 1 mmol) in dichloromethane (6 mL) was added sodium carbonate (0.127 g, 1.2 mmol) and 4-fluorobenzoyl chloride (0.174 g, 1.1 mmol). The mixture was stirred at room temperature for 4 hours. The mixture was concentrated. The residue was purified by chromatography on silica gel (ethyl acetate, then ethyl acetate/methanol=10:1) to give the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.40 (m, 1H), 1.47 (s, 9H), 1.63 (m, 2H), 2.05-2.20 (m, 2H), 2.50-2.65 (m, 2H), 3.00 (m, 2H), 4.20 (m, 2H), 4.70 (m, 1H), 6.68 (m, 1H), 7.10 (m, 2H), 7.80 (m, 2H); MS (ESI) m/z 364 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. customThe residue was purified by chromatography on silica gel (ethyl acetate

Sources & evidence

ORD record
ord-ad35aded5556479b9cda37a401aa44e4
Source dataset
uspto-grants-2014_02
Patent number
US08648074B2

Reaction notes

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