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

HRID 1264590Notes

Reaction equation

HRID 1264590 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-1a1842fcf19c4f92bf81ada5e82839e3
Source dataset
uspto-grants-2003_04
Patent number
US06544984B1

Reaction notes

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