tert-Butanol → HCID 70667141, compound

HRID 516252Notes

Reaction equation

HRID 516252 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH2:12][CH2:13]C(O)=O)[NH:8][C:7](=[O:17])[CH2:6][CH2:5]2.[C:18]([OH:22])([CH3:21])([CH3:20])[CH3:19].C([N:25]([CH2:28]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:37])C=CC=CC=1>O>[C:18]([O:22][C:28](=[O:37])[NH:25][CH2:13][CH2:12][C:11]1[CH:10]=[C:9]2[C:4]([CH2:5][CH2:6][C:7](=[O:17])[NH:8]2)=[CH:3][C:2]=1[I:1])([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 66982568HCID 66982568, compound

Product 1

HCID 70667141HCID 70667141, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 7.87 g of 3-(6-iodo-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)propanoic acid were added 200 ml of t-butanol, 7 ml of triethylamine, and 5 ml of diphenylphosphoryl azide, followed by heating and refluxing for 70 hours. The reaction mixture was cooled to room temperature, then diluted by the addition of water, and stirred, and the solid was collected by filtration and dried to obtain 9.49 g of t-butyl[2-(6-iodo-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)ethyl]carbamate as a pale brown solid. Further, the solid precipitated from the filtrate was collected by filtration to obtain 665 mg of t-butyl[2-(6-iodo-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)ethyl]carbamate as a white solid.

Workup

  1. temperatureby heating
  2. temperaturerefluxing for 70 hours
  3. filtrationthe solid was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-cacab714e02b4cbb9f90197dd2cf89f2
Source dataset
uspto-grants-2015_08
Patent number
US09108977B2

Reaction notes

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