Triphenylphosphine → (S)-2-[4-Dimethylamino-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-N-methoxy-N-methyl-succinamic acid tert-butyl ester

HRID 1814303Notes

Reaction equation

HRID 1814303 reaction equation
[C:1]([O:5][C:6](=[O:29])[C@@H:7]([N:15](O)[S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1N(C)C)(=[O:18])=[O:17])[CH2:8][C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])([CH3:4])([CH3:3])[CH3:2].[N:30]1[C:39]2[C:34](=[C:35]([CH2:40][CH2:41][OH:42])[CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][CH:31]=1.[CH:43]1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[N:62]([C:69](OCC)=O)=NC(OCC)=O>C1COCC1>[C:1]([O:5][C:6](=[O:29])[C@@H:7]([NH:15][S:16]([C:19]1[CH:20]=[CH:21][C:22]([N:62]([CH3:69])[CH3:43])=[CH:23][C:24]=1[O:42][CH2:41][CH2:40][C:35]1[CH:36]=[CH:37][CH:38]=[C:39]2[C:34]=1[CH:33]=[CH:32][CH:31]=[N:30]2)(=[O:18])=[O:17])[CH2:8][C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 225041322-(Quinolin-5-yl)ethan-1-olHCID 86588209(S)-2-(dimethylamino-hydroxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester

Product 1

HCID 86588208(S)-2-[4-Dimethylamino-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-N-methoxy-N-methyl-succinamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-2-(dimethylamino-hydroxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester (0.53 g, 1.20 mmol) in dry THF (30 mL) at 0° C. was added 2-quinolin-5-yl-ethanol (0.22 g, 1.20 mmol) and Ph3P (0.63 g, 2.40 mmol) then followed by drop wise addition of diethyl azodicarboxylate (0.40 mL, 2.40 mmol). The reaction mixture was allowed to warm up to room temperature and stirred for 12 h. The solvent was removed and the crude product was purified using silica gel flash chromatography (20% EtOAc in hexanes). (S)-2-[4-Dimethylamino-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-N-methoxy-N-methyl-succinamic acid tert-butyl ester was obtained (0.57 g, 80%) as an off white foam. MS (APCI) m/z 585.2 (M−1).

Workup

  1. customThe solvent was removed
  2. customthe crude product was purified

Sources & evidence

ORD record
ord-97d15aaffc1544a99e8c808361efc213
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

Loading…