Triphenylphosphine → methyl (S)-2-(4-methanesulfonylpiperazin-1-yl)-3-[4-(2-phenylpyridin-4-ylmethoxy)-benzenesulfonylamino]propanoate

HRID 1966113Notes

Reaction equation

HRID 1966113 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[OH:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([NH:23][CH2:24][C@H:25]([N:30]2[CH2:35][CH2:34][N:33]([S:36]([CH3:39])(=[O:38])=[O:37])[CH2:32][CH2:31]2)[C:26]([O:28][CH3:29])=[O:27])(=[O:22])=[O:21])=[CH:16][CH:15]=1.[C:40]1([C:46]2[CH:51]=[C:50]([CH2:52]O)[CH:49]=[CH:48][N:47]=2)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:39][S:36]([N:33]1[CH2:32][CH2:31][N:30]([C@@H:25]([CH2:24][NH:23][S:20]([C:17]2[CH:18]=[CH:19][C:14]([O:13][CH2:52][C:50]3[CH:49]=[CH:48][N:47]=[C:46]([C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=4)[CH:51]=3)=[CH:15][CH:16]=2)(=[O:21])=[O:22])[C:26]([O:28][CH3:29])=[O:27])[CH2:35][CH2:34]1)(=[O:38])=[O:37]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 16125998(2-Phenylpyridin-4-yl)methanolHCID 86675015methyl (S)-3-(4-hydroxybenzenesulfonylamino)-2-(4-methanesulfonylpiperazin-1-yl)propanoate

Product 1

HCID 86675020methyl (S)-2-(4-methanesulfonylpiperazin-1-yl)-3-[4-(2-phenylpyridin-4-ylmethoxy)-benzenesulfonylamino]propanoateYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.23 ml (1.4 mmol) of diethyl azodicarboxylate is added slowly to a solution of 400 mg (0.9 mmol) of methyl (S)-3-(4-hydroxybenzenesulfonylamino)-2-(4-methanesulfonylpiperazin-1-yl)propanoate (prepared as described in example 5.1), 193 mg (1.0 mmol) of (2-phenylpyridin-4-yl)methanol and 373 mg (1.4 mmol) of triphenylphosphine in 4 ml of tetrahydrofuran. The reaction mixture is stirred for one hour at ambient temperature and then evaporated to dryness. The residue obtained is purified by chromatography on silica gel, elution being carried out with a 60/40 heptane/ethyl acetate mixture. 318 mg (57%) of methyl (S)-2-(4-methanesulfonylpiperazin-1-yl)-3-[4-(2-phenylpyridin-4-ylmethoxy)-benzenesulfonylamino]propanoate are obtained in the form of a white powder.

Workup

  1. customevaporated to dryness
  2. customThe residue obtained
  3. customis purified by chromatography on silica gel, elution

Sources & evidence

ORD record
ord-fa6ff01517d84199bf0e784a07b20a01
Source dataset
uspto-grants-2013_04
Patent number
US08420632B2

Reaction notes

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