Water → HCID 178499707, compound

HRID 1005342Notes

Reaction equation

HRID 1005342 reaction equation
[CH3:1][O:2][C:3]([C:5]([C@H:20]1[CH2:23][C@@H:22]([C:24]([O:26][CH3:27])=[O:25])[CH2:21]1)([CH2:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1)C(O)=O)=[O:4].C([N:30]([CH2:33]C)CC)C.C1C=CC([O:41]P(OC2C=CC=CC=2)(N=[N+]=[N-])=O)=CC=1.O>C1(C)C=CC=CC=1>[N:30]([C:5]([C@H:20]1[CH2:23][C@@H:22]([C:24]([O:26][CH3:27])=[O:25])[CH2:21]1)([CH2:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1)[C:3]([O:2][CH3:1])=[O:4])=[C:33]=[O:41]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 178499703HCID 178499703, compound

Product 1

HCID 178499707HCID 178499707, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of cis-2-methoxycarbonyl-2-(3-methoxy carbonylcyclobutyl)-3-naphthylpropanoic acid (0.25 g, 0.68 mmol), dry triethylamine (72 mg, 0.71 mmol) and diphenylphosphonic azide (0.2 g, 0.71 mmol) in dry toluene (10 ml) was heated with stirring at 80° C. under a nitrogen atmosphere for 20 hours. After cooling the reaction mixture, water was added and the organic phase separated. The aqueous phase was extracted with diethyl ither and the combined organic phases dried, filtered and evaporated to an oil. The crude product was purified by chromatography on flash silica eluting with diethyl ether-hexane (1:1) to give the title compound as a white solid.

Workup

  1. temperaturewas heated
  2. additionwas added
  3. customthe organic phase separated
  4. extractionThe aqueous phase was extracted with diethyl ither
  5. customthe combined organic phases dried
  6. filtrationfiltered
  7. customevaporated to an oil
  8. customThe crude product was purified by chromatography on flash silica eluting with diethyl ether-hexane (1:1)

Sources & evidence

ORD record
ord-dd79cbbf0a524b18a659c2cb3f503a26
Source dataset
uspto-grants-2000_04
Patent number
US06054448

Reaction notes

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