tert-Butanol → HCID 18926568, compound

HRID 1600190Notes

Reaction equation

HRID 1600190 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.C([CH2:21][CH2:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[N:28]([CH2:32][CH2:33][C:34]([O:36][CH3:37])=[O:35])[C:27]([CH3:38])=[C:26]2[CH2:39][C:40]1[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=1)(O)=O.C([N:48]([CH2:51]C)CC)C.[C:53]([OH:57])([CH3:56])([CH3:55])[CH3:54]>>[C:53]([O:57][C:51]([NH:48][CH2:21][CH2:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[N:28]([CH2:32][CH2:33][C:34]([O:36][CH3:37])=[O:35])[C:27]([CH3:38])=[C:26]2[CH2:39][C:40]1[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=1)=[O:8])([CH3:56])([CH3:55])[CH3:54]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 18926567HCID 18926567, compound

Product 1

HCID 18926568HCID 18926568, compound

Conditions

Temperature
100 °C

Procedure

Diphenylphosphoryl azide (3.99 g) was added to a stirred mixture of methyl 5-(2-carboxyethyl)-2-methyl-3-(3-pyridylmethyl)-1H-indole-1-propanoate (5.00 g) and triethylamine (1.46 g) in dry t-butanol (30 ml) and the mixture was heated at 100° C. for 18 hours and then evaporated. Theresidue was dissolved in dichloromethane, and the solution was washed twicewith water and dried (MgSO4). The solvent was evaporated and the residue was chromatographed on silica gel. Elution with dichloromethane and evaporation of the product fractions gave the title compound as a gum (4.51 g), Rf. 0.35(SS4). δ(CDCl3): 1.42(9H,s), 2.37(3H,s), 2.73(2H,t), 2.82(2H,t), 3.36(2H,m), 3.68(3H,s), 4.05(2H,s), 4.39(2H,t), 4.50(1H,br), 7.00(1H,d), 7.10-7.25(3H,m) 7.41 (1H,d), 8.39(1H,d), 8.50(1H,s).

Workup

  1. customevaporated
  2. dissolutionTheresidue was dissolved in dichloromethane
  3. washthe solution was washed twicewith water
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated
  6. customthe residue was chromatographed on silica gel
  7. washElution
  8. customwith dichloromethane and evaporation of the product fractions

Sources & evidence

ORD record
ord-400d1bd55c3641989c893c897d0db2c0
Source dataset
uspto-grants-1998_04
Patent number
US05744488

Reaction notes

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