{Benzyloxycarbonyl-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-ylamino)-ethyl]-amino}-acetic acid ethyl ester → HCID 68554807, compound

HRID 2381923Notes

Reaction equation

HRID 2381923 reaction equation
C(O[C:4](=[O:31])[CH2:5][N:6]([C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[CH2:7][CH2:8][NH:9][N:10]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:20])C>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH2:24]([O:23][C:21]([N:6]1[CH2:7][CH2:8][N:9]([N:10]2[C:11](=[O:20])[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18]2=[O:19])[C:4](=[O:31])[CH2:5]1)=[O:22])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

3

Reactant 1

HCID 68557343{Benzyloxycarbonyl-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-ylamino)-ethyl]-amino}-acetic acid ethyl ester

Product 1

HCID 68554807HCID 68554807, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

A solution of {benzyloxycarbonyl-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-ylamino)-ethyl]-amino}-acetic acid ethyl ester (0.22 g, 0.52 mmol) in diphenyl ether (3 mL) is heated to reflux for 2 h. Diphenyl ether is removed by vacuum distillation and the residue is purified by flash silica gel chromatography (2:1:1 to 1:1:1 heptane:DCM:EtOAc gradient elution) to afford 4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-oxo-piperazine-1-carboxylic acid benzyl ester as a solid (0.126 g, 64%). MS: 380 (M+H); 1H NMR (300 MHz, CDCl3) δ 7.86-7.95 (m, 2H), 7.75-7.86 (m, 2H), 7.24-7.42 (m, 5H), 5.20 (s, 2H), 4.42 (s, 2H), 3.90-4.05 (m, 2H), 3.65-3.87 (m, 2H).

Workup

  1. temperatureto reflux for 2 h
  2. customDiphenyl ether is removed by vacuum distillation
  3. customthe residue is purified by flash silica gel chromatography (2:1:1 to 1:1:1 heptane:DCM:EtOAc gradient elution)

Sources & evidence

ORD record
ord-db4b0784094c407e87c85cb8ca63e793
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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