1,1'-Carbonyldiimidazole → HCID 88054794, compound

HRID 1954346Notes

Reaction equation

HRID 1954346 reaction equation
[NH2:1][C:2]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:10]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:17][C:18](O)=[O:19])[CH:8]=[CH:9]2)[C:3]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22].C1N=CN(C(N2C=NC=C2)=O)C=1.[CH2:38]([O:40][P:41]([CH2:46][O:47][NH2:48])([O:43][CH2:44][CH3:45])=[O:42])[CH3:39]>O1CCCC1>[NH2:1][C:2]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:10]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:17][C:18](=[O:19])[NH:48][O:47][CH2:46][P:41]([O:40][CH2:38][CH3:39])([O:43][CH2:44][CH3:45])=[O:42])[CH:8]=[CH:9]2)[C:3]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 13923039HCID 13923039, compoundHCID 15391985HCID 15391985, compound

Product 1

HCID 88054794HCID 88054794, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.5 mmol of diethyl 2-amino-6-carboxymethyl-azulene-1,3-dicarboxylate in 50 ml of tetrahydrofuran is treated portionwise at 45° C. with 2.5 mmol of N,N-carbonyldiimidazole. The mixture is stirred for 30 minutes, a solution of 2.5 mmol of diethoxyphosphorylmethoxylamine (L. Maier, Phosphorus, Sulphur, and Silicon 1993, Vol. 76, 119-122) in 20 ml of tetrahydrofuran is added and the resulting mixture is heated to reflux for 3 hours. The mixture is concentrated and the residue is chromatographed on silica gel. Elution with isohexane:ethyl acetate 1:1 gives 78% of the title compound of m.p. 146-147° C.

Workup

  1. temperaturethe resulting mixture is heated
  2. temperatureto reflux for 3 hours
  3. concentrationThe mixture is concentrated
  4. customthe residue is chromatographed on silica gel
  5. washElution with isohexane:ethyl acetate 1:1

Sources & evidence

ORD record
ord-c6d7d763b77f4a18863c8534b1e76508
Source dataset
uspto-grants-2000_09
Patent number
US06121322

Reaction notes

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