Triphenylphosphine → Methyl 3-(4-{[4-(chloromethyl)benzyl][(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate

HRID 507909Notes

Reaction equation

HRID 507909 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:16][CH:15]=1)(=[O:12])=[O:11])([O-:3])=[O:2].[Cl:26][CH2:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32]O)=[CH:30][CH:29]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1>[Cl:26][CH2:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][N:13]([S:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11])[C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:16][CH:15]=2)=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5107660[4-(Chloromethyl)phenyl]methanolHCID 23157467Methyl 3-(4-{[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate

Product 1

HCID 23157281Methyl 3-(4-{[4-(chloromethyl)benzyl][(2-nitrophenyl)sulfonyl]amino}phenyl)propanoateYield 95.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of methyl 3-(4-{[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate (2.78 g, 7.63 mmol), 4-chloromethylbenzyl alcohol (1.21 g, 7.70 mmol) and triphenylphosphine (3.93 g, 15.4 mmol) in toluene (150 mL) was stirred under ice-cooling. Diethyl azodicarboxylate (40% toluene solution, 6.98 μmL, 15.4 mmol) was added, and the mixture was allowed to warm to room temperature and stirred for 72 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (20%-60% ethyl acetate/hexane). Hexane-ethyl acetate was added to the obtained residue, and the resultant insoluble material was filtered off. The filtrate was concentrated to give the title compound (3.65 g, yield 95%) as a red oil.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (20%-60% ethyl acetate/hexane)
  4. additionHexane-ethyl acetate was added to the obtained residue
  5. filtrationthe resultant insoluble material was filtered off
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-bec1acceaea242e2aa009d7f2137bcb3
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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