Triphenylphosphine → Triphenylphosphine Oxide

HRID 1814281Notes

Reaction equation

HRID 1814281 reaction equation
[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[OH:25])(=[O:18])=[O:17])[C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])([CH3:4])([CH3:3])[CH3:2].[CH:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]([CH2:37][CH2:38][OH:39])=[CH:29][N:28]=1.[C:40]1([P:46]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.N(C(OCC)=O)=NC(OCC)=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][CH2:38][CH2:37][C:30]1[C:31]2[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:27]=[N:28][CH:29]=1)(=[O:18])=[O:17])[C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])([CH3:4])([CH3:2])[CH3:3].[C:53]1([P:46](=[O:39])([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 225040102-(Isoquinolin-4-yl)ethanolHCID 86588199(S)-3-(2-hydroxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester

Product 2

HCID 13097Triphenylphosphine OxideHCID 86588200(S)-3-[2-(2-isoquinolin-4-yl-ethoxy)-benzenesulfonylamino]-N-methoxy-N-methyl-succinamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To (S)-3-(2-hydroxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester (194 mg, 0.50 mmol), 2-isoquinolin-4-yl-ethanol (108 mg, 0.625 mmol), triphenyl phosphine (197 mg, 0.75 mmol) in THF(5 mL) was added diethyl azodicarboxylate (133 μL, 0.85 mmol). After 16 h the solvent was removed under reduced pressure, the residue was chromatographed on silica gel 20% THF in dichloromethane to give (S)-3-[2-(2-isoquinolin-4-yl-ethoxy)-benzenesulfonylamino]-N-methoxy-N-methyl-succinamic acid tert-butyl ester as a colorless foam (394 mg, contaminated with triphenyl phosphine oxide). MS (APCI) m/z 544.1 (M+1).

Workup

  1. customAfter 16 h the solvent was removed under reduced pressure
  2. customthe residue was chromatographed on silica gel 20% THF in dichloromethane

Sources & evidence

ORD record
ord-6971f3e552ef42528ee7f7003d8c4a62
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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