Isopropanol → N-(4-{[2-({6-[(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethoxy]methyl}phenyl)-N'-phenylurea

HRID 2116986Notes

Reaction equation

HRID 2116986 reaction equation
[NH2:1][C:2]1[CH:36]=[CH:35][C:5]([CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]2[CH2:21][C@@H:20]([C:22]3[CH:33]=[CH:32][C:25]4[O:26][C:27]([CH3:31])([CH3:30])[O:28][CH2:29][C:24]=4[CH:23]=3)[O:19][C:18]2=[O:34])=[CH:4][CH:3]=1.[C:37]1([N:43]=[C:44]=[O:45])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(O)(C)C>ClCCl>[CH3:31][C:27]1([CH3:30])[O:26][C:25]2[CH:32]=[CH:33][C:22]([C@H:20]3[O:19][C:18](=[O:34])[N:17]([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][O:10][CH2:9][CH2:8][O:7][CH2:6][C:5]4[CH:4]=[CH:3][C:2]([NH:1][C:44]([NH:43][C:37]5[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=5)=[O:45])=[CH:36][CH:35]=4)[CH2:21]3)=[CH:23][C:24]=2[CH2:29][O:28]1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 7672Phenyl isocyanateHCID 66845317(5R)-3-(6-{2-[(4-aminobenzyl)oxy]ethoxy}hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

Product 1

HCID 66845075N-(4-{[2-({6-[(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethoxy]methyl}phenyl)-N'-phenylurea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (5R)-3-(6-{2-[(4-aminobenzyl)oxy]ethoxy}hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (150 mg) in dichloromethane (5 ml) under nitrogen was treated with phenyl isocyanate (0.07 ml) and the mixture stirred at 20° for 5 h. Isopropyl alcohol (5 ml) was added and the solution was stirred for a further 18 h. The solvent was evaporated in vacuo and the residue purified by SPE (silica, 10 g). Elution with EtOAc-cyclohexane (3:7) then EtOAc gave the title compound (159 mg). LCMS RT=3.68 min.

Workup

  1. stirringthe solution was stirred for a further 18 h
  2. customThe solvent was evaporated in vacuo
  3. customthe residue purified by SPE (silica, 10 g)
  4. washElution with EtOAc-cyclohexane (3:7)

Sources & evidence

ORD record
ord-90f4f5c377294205b4afde49a047cc0f
Source dataset
uspto-grants-2008_10
Patent number
US07439393B2

Reaction notes

Loading…