Benzyl succinimido carbonate → HCID 57842840, compound

HRID 735670Notes

Reaction equation

HRID 735670 reaction equation
[C:1](=[O:18])(ON1C(=O)CCC1=O)[O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N+:19]([C:22]1[CH:23]=[C:24]([C@H:28]([NH2:30])[CH3:29])[CH:25]=[CH:26][CH:27]=1)([O-:21])=[O:20]>C(Cl)Cl.CN(C=O)C>[N+:19]([C:22]1[CH:23]=[C:24]([C@H:28]([NH:30][C:1](=[O:18])[O:2][CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH3:29])[CH:25]=[CH:26][CH:27]=1)([O-:21])=[O:20]

Participants

5

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 40427003HCID 40427003, compound

Product 1

HCID 57842840HCID 57842840, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl 2,5-dioxopyrrolidin-1-yl carbonate (4.95 g, 19.9 mmol) and TEA (10 mL) in DCM (50 mL) was added a solution of (R)-1-(3-nitrophenyl)ethanamine (3 g, 18 mmol) in DMF (10 mL). The mixture was stirred 2 h and quenched with water (50 mL). The organic layer was separated and dried (MgSO4) before concentrating in vacuo. The residue was purified by flash chromatography (0-35% EtoAc/Hexane) to afford 64A (5 g, 93%) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.50 (d, J=6.59 Hz, 3 H) 4.87-4.98 (m, 1 H) 5.00-5.15 (m, 2 H) 7.34 (s, 5 H) 7.49 (t, J=7.69 Hz, 1 H) 7.64 (d, J=7.03 Hz, 1 H) 8.11 (d, J=7.91 Hz, 1 H) 8.17 (s, 1 H).

Workup

  1. customquenched with water (50 mL)
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. concentrationbefore concentrating in vacuo
  5. customThe residue was purified by flash chromatography (0-35% EtoAc/Hexane)

Sources & evidence

ORD record
ord-39d3814bb84e434eb56e76a638c31832
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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