Benzyl succinimido carbonate → HCID 66746504, compound

HRID 2410155Notes

Reaction equation

HRID 2410155 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][C:12]([NH2:15])([CH3:14])[CH3:13])[C:3]=1[C:4]#[N:5].C([O-])(O)=O.[Na+].[C:21](=O)([O:30]N1C(=O)CCC1=O)[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1.O>[NH2:1][C:2]1[C:3]([C:4]#[N:5])=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][CH2:11][C:12]([NH:15][C:21](=[O:30])[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 83172Benzyl succinimido carbonateHCID 516892Sodium BicarbonateHCID 667465182-amino-6-(2-amino-2-methylpropoxy)benzonitrile

Product 1

HCID 66746504HCID 66746504, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 2-amino-6-(2-amino-2-methylpropoxy)benzonitrile (Example Dd, 30.5 g, 148.6 mmol) in THF/H2O (1:1, 400 mL) was added NaHCO3 (24.7 g, 294 mmol), followed by benzyl (2,5-dioxopyrrolidin-1-yl) carbonate (44.0 g, 176 mmol) at room temperature. The reaction was stirred at room temperature for 4 h then the organic layer was separated and the aqueous layer was extracted with EtOAc (2×). The combined organic layers were washed with brine and dried over MgSO4. After filtration, the solvent was evaporated and the crude oil was purified by chromatography on silica gel (eluent: 0-60% EtOAc in hexane) to give the title compound as yellow oil (44.8 g, 89%). 1H NMR (400 MHz, DMSO-d6) δ 1.30 (s, 6H), 4.02 (s, 2H), 4.96 (s, 2H), 5.98 (s, 2H), 6.14 (d, J=8.0 Hz, 1H), 6.32 (dd, J=0.8, 8.4 Hz, 1H), 7.12 (t, J=8.4 Hz, 1H), 7.38-7.21 (m, 6H). MS 340 (MH+).

Workup

  1. customthe organic layer was separated
  2. extractionthe aqueous layer was extracted with EtOAc (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtration
  6. customthe solvent was evaporated
  7. customthe crude oil was purified by chromatography on silica gel (eluent: 0-60% EtOAc in hexane)

Sources & evidence

ORD record
ord-ea559df170934625b9446ac388718728
Source dataset
uspto-grants-2014_08
Patent number
US08815956B2

Reaction notes

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