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Triphenylphosphine → 3-[4-acetylamino-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-N-methoxy-N-methyl-succinamic acid tert-butyl ester

HRID 1814297
Notes
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Reaction equation

HRID 1814297 reaction equation
[C:1]([O:5][C:6](=[O:30])[CH2:7][CH:8]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:28])[CH3:27])=[CH:21][C:20]=1[OH:29])(=[O:18])=[O:17])[C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])([CH3:4])([CH3:3])[CH3:2].[N:31]1[C:40]2[C:35](=[C:36]([CH2:41][CH2:42]O)[CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([O:5][C:6](=[O:30])[CH2:7][CH:8]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:28])[CH3:27])=[CH:21][C:20]=1[O:29][CH2:42][CH2:41][C:36]1[CH:37]=[CH:38][CH:39]=[C:40]2[C:35]=1[CH:34]=[CH:33][CH:32]=[N:31]2)(=[O:18])=[O:17])[C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])([CH3:4])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 225041322-(Quinolin-5-yl)ethan-1-olHCID 865882053-(4-acetylamino-2-hydroxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester

Product 1

HCID 865882063-[4-acetylamino-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-N-methoxy-N-methyl-succinamic acid tert-butyl ester
Yield 83.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

3-(4-Acetylamino-2-hydroxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester (0.40 g, 0.9 mmol) was combined with 2-Quinolin-5-yl-ethanol (0.155 g, 0.9 mmol) and triphenyl phosphine (355 mg, 1.3 mmol) in 15 mL THF. The solution was cooled to 0° C. DEAD (0.21 mL, 1.3 mmol) was added. The reaction was slowly warmed to room temperature, and stirred overnight. The reaction mixture was concentrated in vacuo. The crude product was chromatorgraphed using 1:1 ethyl acetate/hexanes followed by ethyl acetate, and then 10% methanol in ethyl acetate to yield 3-[4-acetylamino-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-N-methoxy-N-methyl-succinamic acid tert-butyl ester 450 mg (83%) of an off-white solid. MS (APCI) m/z 601.2 (M+1).

Workup

  1. temperatureThe reaction was slowly warmed to room temperature
  2. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-52e8ae22065142348375f4dbe1377f90
Source dataset
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06875765B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes