Triethylamine → HCID 21713091, compound

HRID 2288174Notes

Reaction equation

HRID 2288174 reaction equation
C([O:5][C:6]([CH2:8][O:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=1[CH:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH2:28][CH2:29][CH3:30])[CH:25]=2)[CH:20]([C:31]2[CH:36]=[CH:35][C:34]3[O:37][CH2:38][O:39][C:33]=3[CH:32]=2)[CH:19]1C(O)=O)=[O:7])(C)(C)C.C([N:45](CC)CC)C>C1C=CC=CC=1.O1CCOCC1>[NH2:45][CH:19]1[CH:18]([C:11]2[CH:12]=[CH:13][C:14]([O:16][CH3:17])=[CH:15][C:10]=2[O:9][CH2:8][C:6]([OH:5])=[O:7])[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH2:28][CH2:29][CH3:30])[CH:25]=2)[CH:20]1[C:31]1[CH:36]=[CH:35][C:34]2[O:37][CH2:38][O:39][C:33]=2[CH:32]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 18703882HCID 18703882, compound

Product 1

HCID 21713091HCID 21713091, compoundYield 45.2%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

(1RS,2SR,3RS)-3-(2-tert-butoxycarbonylmethoxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylic acid (100 mg, 0.18 mmol), triphenylphosphonyl azide (0.03 ml, 0.18 mmol), and triethylamine (73 mg, 0.72 mmol) were dissolved in dry benzene (4 ml) and heated at 40° C. for 2 h and at 75° C. for 2 h. The reaction mixture was then partitioned between 1 N HCl and ethyl acetate. The organic layer was washed with water and brine, dried (MgSO4 anhyd.), filtered and evaporated to give the corresponding isocianate as a colorless oil. After purification by column chromatography (silica gel, ethyl acetate/hexane 30:70), the isocianate (100 mg) thus obtained was dissolved in 1 M HC1 in dioxane (3 mL) and the mixture was heated at 80° C. overnight. The solvent was removed in vacuo, the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4) and concentrated to give a colorless oil that was purified by HPLC (1:1 CNCH3 :H2O (containig 0.1% TFA)) to produce the desired product (40 mg, 42%) as an off-white solid, m.p. 181-182° C. (dec).

Workup

  1. customThe reaction mixture was then partitioned between 1 N HCl and ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried (MgSO4 anhyd.)
  4. filtrationfiltered
  5. customevaporated
  6. customto give the corresponding isocianate as a colorless oil
  7. customAfter purification by column chromatography (silica gel, ethyl acetate/hexane 30:70)
  8. customthe isocianate (100 mg) thus obtained
  9. temperaturethe mixture was heated at 80° C. overnight
  10. customThe solvent was removed in vacuo
  11. customthe residue was partitioned between ethyl acetate and water
  12. washThe organic layer was washed with brine
  13. dry with materialdried (MgSO4)
  14. concentrationconcentrated
  15. customto give a colorless oil that
  16. customwas purified by HPLC (1:1 CNCH3 :H2O (containig 0.1% TFA))

Sources & evidence

ORD record
ord-cc8f914585ad42679286fb9eae0bf86e
Source dataset
uspto-grants-2000_07
Patent number
US06087389

Reaction notes

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