Methanol → HCID 13134738, compound

HRID 496055Notes

Reaction equation

HRID 496055 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.[CH3:18][O:19][C:20]([C:22]1(C(O)=O)[CH2:24][CH2:23]1)=[O:21].[CH3:28][OH:29].C([N:32]([CH2:35]C)CC)C>C1(C)C=CC=CC=1>[CH3:28][O:29][C:35]([NH:32][C:22]1([C:20]([O:19][CH3:18])=[O:21])[CH2:23][CH2:24]1)=[O:8]

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 138618231-(Methoxycarbonyl)cyclopropane-1-carboxylic acid

Product 1

HCID 13134738HCID 13134738, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

300 g of diphenylphosphoryl azide are added to a solution, heated to 80° C., of 1.09 mol of the compound obtained in Step 1 in 1.09 liters of toluene and 153 ml of triethylamine. The reaction is markedly exothermic. When all evolution of gas has ceased, the reaction mixture is cooled to 50° C., 66.3 ml of methanol are added, and the mixture is again heated at 70° C. for 2 hours. After cooling and conventional treatment, chromatography over silica gel (dichloromethane/methanol: 97/3) allows the expected product to be isolated.

Workup

  1. temperaturethe mixture is again heated at 70° C. for 2 hours
  2. temperatureAfter cooling

Sources & evidence

ORD record
ord-b503db7e746647f09f2645952bedafec
Source dataset
uspto-grants-2005_09
Patent number
US06943184B2

Reaction notes

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