tert-Butanol → HCID 58494612, compound

HRID 516241Notes

Reaction equation

HRID 516241 reaction equation
[O:1]=[C:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([CH2:12][CH2:13]C(O)=O)=[CH:7][CH:8]=2)[NH:3]1.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:24])=CC=1.C([N:36]([CH2:39]C)CC)C.[C:41]([OH:45])([CH3:44])([CH3:43])[CH3:42]>>[C:41]([O:45][C:39](=[O:24])[NH:36][CH2:13][CH2:12][C:6]1[CH:5]=[C:4]2[C:9]([CH2:10][CH2:11][C:2](=[O:1])[NH:3]2)=[CH:8][CH:7]=1)([CH3:44])([CH3:43])[CH3:42]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 2749816HCID 2749816, compound

Product 1

HCID 58494612HCID 58494612, compound

Conditions

Temperature
100 °C

Procedure

To a suspension of 2 g of 3-(2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)propionic acid in 40 ml of t-butanol were added 2.1 ml of DPPA and 2.6 ml of triethylamine, followed by heating and refluxing at 100° C. for 18 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel chromatography (elution solvent: chloroform-MeOH) to obtain 1.832 g of t-butyl[2-(2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)ethyl]carbamate as an orange solid.

Workup

  1. temperatureby heating
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel chromatography (elution solvent: chloroform-MeOH)

Sources & evidence

ORD record
ord-136ca925f9ff4bbf8f56c95e60d5bc4a
Source dataset
uspto-grants-2015_08
Patent number
US09108977B2

Reaction notes

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