ethyl N-ethoxycarbonyliminocarbamate → HCID 91115529, compound

HRID 2222878Notes

Reaction equation

HRID 2222878 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[CH3:13][C:14]([CH3:38])([CH3:37])[CH2:15][O:16][C:17]([NH:19][C@@H:20]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[C:29]([N+:34]([O-:36])=[O:35])[CH:28]=1)[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:18].O[CH:40]([CH2:62][CH2:63][CH3:64])[CH:41]([C:52]([O:54][CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)=[O:53])[C:42]([O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:43]>C1COCC1>[CH3:38][C:14]([CH3:37])([CH3:13])[CH2:15][O:16][C:17]([NH:19][C@H:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][C@H:40]([CH2:62][CH2:63][CH3:64])[CH:41]([C:52]([O:54][CH2:55][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)=[O:53])[C:42]([O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[O:43])=[C:29]([N+:34]([O-:36])=[O:35])[CH:28]=1)=[O:18]

Participants

5

Reactant 3

HCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 58664764HCID 58664764, compoundHCID 69142683HCID 69142683, compound

Product 1

HCID 91115529HCID 91115529, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5.43 g of polymer-bound DEAD (diethyl azodicarboxylate) in 30 ml of THF are added to a solution of 4 g of 12 and 5.35 g of dibenzyl 2-hydroxypentanedicarboxylate (X) in anhydrous THF. The mixture is shaken for 16 hours. The polymer is separated off, and the solvent is removed. The residue is taken up in ethyl acetate, and conventional work-up gives 13, which is not purified further for the further reaction.

Workup

  1. customThe polymer is separated off
  2. customthe solvent is removed

Sources & evidence

ORD record
ord-0ee98cc986704b94a7455cd4fe020a8b
Source dataset
uspto-grants-2008_05
Patent number
US07371854B2

Reaction notes

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