Succinic anhydride → HCID 46867131, compound

HRID 1627200Notes

Reaction equation

HRID 1627200 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][NH:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH3:2].[C:16]1(=[O:22])[O:21][C:19](=[O:20])[CH2:18][CH2:17]1>CN(C=O)C>[C:11]([O:10][C:8]([NH:7][N:6]([C:16](=[O:22])[CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:15])=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 13434344Tert-butyl 2-(2-ethoxy-2-oxoethyl)hydrazine-1-carboxylate

Product 1

HCID 46867131HCID 46867131, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

Into a solution of (N′-tert-Butoxycarbonyl-hydrazino)-acetic acid ethyl ester 4 (1.85 g, 18.5 mmol) in DMF (30 mL) was added succinic anhydride (4.84 g, 22.2 mmol) and the mixture was stirred at 75° C. for 18 h. DMF was evaporated and the crude mixture was purified by flash column chromatography using hexane:ethylacetate (1% acetic acid) as an eluent (yield 50%). 1H NMR (500 MHz, CDCl3) 1.28 (3H, CH2—CH3, t), 1.48 (9H, C—CH3, s), 2.55-3.00 (6H, NH—CH2—CO, N—CH2—CH2—CO, m), 4.20 (2H, CH2CH3, q); MS Anal. Mol. Wt. 318.25 (M−1).

Workup

  1. customDMF was evaporated
  2. customthe crude mixture was purified by flash column chromatography

Sources & evidence

ORD record
ord-8ab5c2ead79846df8ab4de5e764b98ad
Source dataset
uspto-grants-2014_07
Patent number
US08785499B2

Reaction notes

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