Triethylamine → HCID 54031289, compound

HRID 1903222Notes

Reaction equation

HRID 1903222 reaction equation
C([C@@H:4]1[CH2:6][C@H:5]1[S:7][C:8]1[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])C=CC=CC=1.C([N:43]([CH2:46]C)CC)C.[CH3:48][Si:49]([CH3:54])([CH3:53])[CH2:50][CH2:51][OH:52]>C1(C)C=CC=CC=1>[CH3:48][Si:49]([CH3:54])([CH3:53])[CH2:50][CH2:51][O:52][C:46]([NH:43][C@@H:4]1[CH2:6][C@H:5]1[S:7][C:8]1[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)=[O:31]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 180132-(Trimethylsilyl)ethanolHCID 199401P,P-Diphenylphosphinic azideHCID 54424676HCID 54424676, compound

Product 1

HCID 54031289HCID 54031289, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-(trans-2-carboxycyclopropylthio)-3-phenylquinoline (3.26 g.), diphenylphosphoryl azide (2.21 ml.) and triethylamine (1.43 ml.) in dry toluene (65 ml.) was stirred under argon for 2 hr. at 90°. 2-(Trimethylsilyl)ethanol (1.53 ml.) was added, and the reaction mixture was stirred for a further 16 hr. at 90°. The mixture was cooled to ambient temperature, washed with water (2×20 ml.), dried (Na2SO4), and the toluene removed under reduced pressure. The residual brown oil (5.5 g.) was purified on a basic alumina column (200 gm. Brockmann Grade III) by elution with 20% v/v chloroform in petroleum ether to give 2-{trans-2-[2-(trimethylsilyl)ethoxycarbonylamino]cyclopropylthio}-3-phenylquinoline as a light yellow oil, which was characterised by mass spectrometry, molecular ion equals 436, and by NMR (CDCl3 solution, 90 MHz) multiplet 2.5 δ (2H, cyclopropane methine).

Workup

  1. customat 90°
  2. customat 90°
  3. washwashed with water (2×20 ml.)
  4. dry with materialdried (Na2SO4)
  5. customthe toluene removed under reduced pressure
  6. customThe residual brown oil (5.5 g.) was purified on a basic alumina column (200 gm. Brockmann Grade III) by elution with 20% v/v chloroform in petroleum ether

Sources & evidence

ORD record
ord-2d18b80f2ec44f8caeea3b5e9e8b8a3a
Source dataset
uspto-grants-1984_03
Patent number
US04435405

Reaction notes

Loading…