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

HRID 1814332
Notes
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Reaction equation

HRID 1814332 reaction equation
[C:1]([O:5][C:6](=[O:29])[CH2:7][CH:8]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([C:25](=[O:27])[NH2:26])=[CH:21][C:20]=1[OH:28])(=[O:18])=[O:17])[C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:49]1[C:58]2[C:53](=[C:54]([CH2:59][CH2:60]O)[CH:55]=[CH:56][CH:57]=2)[CH:52]=[CH:51][CH:50]=1.N(C(OCC)=O)=NC(OCC)=O>C(Cl)Cl>[C:1]([O:5][C:6](=[O:29])[CH2:7][CH:8]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([C:25](=[O:27])[NH2:26])=[CH:21][C:20]=1[O:28][CH2:60][CH2:59][C:54]1[CH:55]=[CH:56][CH:57]=[C:58]2[C:53]=1[CH:52]=[CH:51][CH:50]=[N:49]2)(=[O:18])=[O:17])[C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 225041322-(Quinolin-5-yl)ethan-1-olHCID 865882283-(4-carbamoyl-2-hydroxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester

Product 1

HCID 865882273-[4-carbamoyl-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-N-methoxy-N-methyl-succinamic acid tert-butyl ester
Yield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a methylene chloride solution of 3-(4-carbamoyl-2-hydroxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester at room temperature was added triphenylphosphine (0.25 g, 0.95 mmol), 2-quinolin-5-yl-ethanol (0.11 g, 0.66 mmol) and diethyl azodicarboxylate (0.17 ml, 1.12 mmol). The reaction was stirred at room temperature for 3 days. The reaction was then concentrated under reduced pressure. The crude residue was chromatographed [silica gel with a gradient of 100% ethyl acetate to 10% (1:9 NH4OH/ethanol) in ethyl acetate] to give 3-[4-carbamoyl-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-N-methoxy-N-methyl-succinamic acid tert-butyl ester as a white foam (0.27 g, 69%). 1H NMR(300 MHz, DMSO) 8.90 (d, 1H), 8.73 (d, 1H), 8.08 (s, 1H), 7.93 (d, 1H), 7.62 (m, 8H), 4.43 (m, 3H), 3.71 (m, 2H), 3.47 (bs, 3H), 2.77 (bs, 3H), 2.54 (dd, 1H), 2.34 (dd, 1H), 1.31 (s, 9H). MS(APCI) m/z 585.1 (M−H), 587.1 (M+1).

Workup

  1. concentrationThe reaction was then concentrated under reduced pressure
  2. customThe crude residue was chromatographed [silica gel with a gradient of 100% ethyl acetate to 10% (1:9 NH4OH/ethanol) in ethyl acetate]

Sources & evidence

ORD record
ord-f2ccde94e3894e6ea47587d8ceec14d7
Source dataset
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06875765B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes