Succinic anhydride → HCID 86628342, compound

HRID 1672098Notes

Reaction equation

HRID 1672098 reaction equation
[CH3:1][N:2]([C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])[OH:3].[C:11]1(=[O:17])[O:16][C:14](=[O:15])[CH2:13][CH2:12]1>CN(C1C=CN=CC=1)C.[Cl-].[NH4+]>[C:7]([O:6][C:4]([N:2]([CH3:1])[O:3][C:11](=[O:17])[CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[O:5])([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 2

HCID 7922Succinic anhydrideHCID 272414tert-Butyl hydroxy(methyl)carbamate

Product 1

HCID 86628342HCID 86628342, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of N-methyl-N-boc hydroxylamine 3 (536 mg, 3.65 mmol) in ichloromethane (8 mL) were added DMAP (134 mg, 1.10 mmol) and succinic anhydride (548 mg, 5.48 mmol). The resulting mixture was stirred for 16 h at room temperature. The reaction mixture was poured into a saturated solution of ammonium chloride (10 mL) and extracted with ethyl acetate (2×40 mL). The combined organic layer was washed with water (20 mL) and dried over sodium sulfate. The solvent was removed in vacuo and the crude product was purified by silica flash column chromatography using 45% EtOAc/hexane as eluent to give the corresponding acid as a white solid (693 mg, 2.81 mmol, 77%). 1H NMR (CDCl3, 400 MHz): δ (ppm) 1.42 (s, 9H), 2.65-2.70 (m, 4H), 3.17 (s, 3H).

Workup

  1. extractionextracted with ethyl acetate (2×40 mL)
  2. washThe combined organic layer was washed with water (20 mL)
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed in vacuo
  5. customthe crude product was purified by silica flash column chromatography

Sources & evidence

ORD record
ord-1e3e7f4611d442fcbc576cb22a2fe7c3
Source dataset
uspto-grants-2011_08
Patent number
US07998486B2

Reaction notes

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