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

HRID 1814352Notes

Reaction equation

HRID 1814352 reaction equation
[C:1]([O:5][C:6](=[O:26])[CH2:7][CH:8]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[OH:25])(=[O:18])=[O:17])[C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])([CH3:4])([CH3:3])[CH3:2].[N:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][C:28]=1CCO.[C:40]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:41]=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([O:5][C:6](=[O:26])[CH2:7][C@H:8]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH2:40][CH2:41][C:32]1[CH:33]=[CH:34][CH:35]=[C:36]2[C:31]=1[CH:30]=[CH:29][CH:28]=[N:27]2)(=[O:18])=[O:17])[C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 705322-QuinolineethanolHCID 5462977Diethyl azodicarboxylateHCID 865882353-(2-hydroxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester

Product 1

HCID 86588234(S)-N-methoxy-N-methyl-3-[2-(2-quinolin-5-yl-ethoxy)benzenesulfonylamino]-succinamic acid tert-butyl esterYield 126.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of S)-3-(2-hydroxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester (2.0 g, 5.15 mmol), quinoline ethanol (0.892 g, 5.15 mmol) and triphenylphospine (2.02 g, 7.73 mmol) in 80 mL of THF at 0° C. was slowly added DEAD (1.22 mL, 7.73 mmol). The reaction was stirred for 17 h with slow warming to RT before removing the solvent. The residue was chromatographed (250 g SiO2-50% EtOAC/Hex) to afford 3.55 g of (S)—N-methoxy-N-methyl-3-[2-(2-quinolin-5-yl-ethoxy)benzenesulfonylamino]-succinamic acid tert-butyl ester (contaminated with some triphenylphosphine oxide). 1H NMR (400 MHz, CDCl3) 8.90(d, 1H, J=4 Hz), 8.61(d, 1H, J=8 Hz), 8.04(d, 1H, J=8 Hz), 7.81(d, 1H, J=8 Hz), 7.69(t, 1H, J=8 Hz), 7.65(t, 1H, J=8 Hz), 7.51(t, 1H, J=8 Hz), 7.49(d, 1H, J=8 Hz), 6.95(t, 1H, J=8 Hz), 6.85(d, 1H, J=8 Hz), 5.90(d, 1H, J=10 Hz), 4.38(m, 1H), 3.90-3.65(m, 2H), 3.45(s, 3H), 2.80(s, 3H), 2.40(ABX, AB portion, 2H, JAB=15, JAX=6, JBX=7, ΔνAB=50.3 Hz), 1.41(s, 9H).

Workup

  1. customat 0° C.
  2. custombefore removing the solvent
  3. customThe residue was chromatographed (250 g SiO2-50% EtOAC/Hex)

Sources & evidence

ORD record
ord-c80f586342894664a48d7cef50ad5065
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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