Succinic anhydride → 3-(Bis(((t-butyloxy)carbonyl)methyl)carbamoyl)propanoic acid

HRID 1397110Notes

Reaction equation

HRID 1397110 reaction equation
[C:1]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:12])[CH2:2][NH:3][CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[C:18]1(=[O:24])[O:23][C:21](=[O:22])[CH2:20][CH2:19]1.C(N(C(C)C)C(C)C)C>C(Cl)(Cl)Cl.ClCCl>[C:14]([O:13][C:1]([CH2:2][N:3]([CH2:4][C:5]([O:7][C:8]([CH3:10])([CH3:9])[CH3:11])=[O:6])[C:18]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[O:24])=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 7922Succinic anhydrideHCID 81531DiisopropylethylamineHCID 4393691DI-T-Butyl iminodiacetate

Product 1

HCID 866665243-(Bis(((t-butyloxy)carbonyl)methyl)carbamoyl)propanoic acidYield 72.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Compound 14 (0.88 g, 3.59 mmol), succinic anhydride (0.377 g, 3.77 mmol), ethyldiisopropylamine (625 μL, 3.59 mmol) and 4-di(methylamino)pyridine (44 mg, 0.359 mmol) were dissolved in CHCl3 (15 mL) and stirred for 48 h. The mixture was diluted with dichloromethane (140 mL) and the organic layer was washed with H2O (2×75 mL) and saturated aqueous NaCl, dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by silica gel chromatography (80% EtOAc in hexanes) to give the compound 15 (0.9 g, 72.6%). 1H NMR (400 MHz, CDCl3) δ 1.44 (s, 9H), 1.47 (s, 9H), 2.62 (t, J=5.8, 2H), 2.69 (t, J=5.8, 2H), 4.02 (s, 2H), 4.06 (s, 2H). ESI-MS calculated for C16H27NO7, 345.59 found 368.1 (M+Na).

Workup

  1. washthe organic layer was washed with H2O (2×75 mL) and saturated aqueous NaCl
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude material was purified by silica gel chromatography (80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-1418035c9c3440b891b7576b7d241d9d
Source dataset
uspto-grants-2014_12
Patent number
US08901072B2

Reaction notes

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