Triphenylphosphine → N-[(4-Chloro-2-nitrophenyl)methyl]-N-[(4-methoxyphenyl)sulfonyl]-O-(tetrahydro-2H-pyran-2-yl)serine methyl ester

HRID 1420599Notes

Reaction equation

HRID 1420599 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C@H:13]([C:22]([O:24][CH3:25])=[O:23])[CH2:14][O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[Cl:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31]O)=[C:29]([N+:35]([O-:37])=[O:36])[CH:28]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[O:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH:16]1[O:15][CH2:14][CH:13]([N:12]([S:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)(=[O:10])=[O:11])[CH2:31][C:30]1[CH:33]=[CH:34][C:27]([Cl:26])=[CH:28][C:29]=1[N+:35]([O-:37])=[O:36])[C:22]([O:24][CH3:25])=[O:23]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 899564-Chloro-2-nitrobenzyl alcoholHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 131721840HCID 131721840, compound

Product 1

HCID 18613000N-[(4-Chloro-2-nitrophenyl)methyl]-N-[(4-methoxyphenyl)sulfonyl]-O-(tetrahydro-2H-pyran-2-yl)serine methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 1.67 g (4.4 mmol) of (D,L) N-(4-methoxybenzenesulfonyl)-O-(2-tetrahydropyranyl) serine, methyl ester, 0.825 g, (4.4 mol) of 4-chloro-2-nitrobenzyl alcohol and 1.16 g (4.4 mmol) of triphenylphosphine in 4.5 ml of tetrahydrofuran was added dropwise a solution of 0.766 g (4.4 mmol) of diethyl azodicarboxylate in 1 ml of tetrahydrofuran. The mixture was stirred at room temperature overnight and the solvent removed under vacuum. The residue was triturated with diethyl ether, filtered and the filtrate passed through a thin pad of hydrous magnesium silicate. The pad was washed with ethyl acetate and the total filtrate concentrated to dryness under vacuum to give 4.54 g of solid. The solid was chromatographed on silica gel with hexane-ethyl acetate (55:45) as solvent. The fractions containing product were combined and the solvent removed to give 0.55 g of oily solid; Mass spectrum (ES) 543.1 (M+H).

Workup

  1. customthe solvent removed under vacuum
  2. customThe residue was triturated with diethyl ether
  3. filtrationfiltered
  4. washThe pad was washed with ethyl acetate
  5. concentrationthe total filtrate concentrated to dryness under vacuum

Sources & evidence

ORD record
ord-345656e455e04cc2982fddc6c6c3d16f
Source dataset
uspto-grants-2000_06
Patent number
US06071903

Reaction notes

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