Triphenylphosphine → methyl 3-[4-([(2-nitrophenyl)sulfonyl]{4-[(2-phenyl-1H-indol-1-yl)methyl]benzyl}amino)phenyl]propanoate

HRID 508026Notes

Reaction equation

HRID 508026 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].[C:26]1([C:32]2[N:33]([CH2:41][C:42]3[CH:47]=[CH:46][C:45]([CH2:48]O)=[CH:44][CH:43]=3)[C:34]3[C:39]([CH:40]=2)=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]([CH2:48][C:45]1[CH:44]=[CH:43][C:42]([CH2:41][N:33]2[C:34]3[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH:40]=[C:32]2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:47][CH:46]=1)[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]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 23111705{4-[(2-phenyl-1H-indol-1-yl)methyl]phenyl}methanolHCID 23157467Methyl 3-(4-{[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate

Product 1

HCID 23157671methyl 3-[4-([(2-nitrophenyl)sulfonyl]{4-[(2-phenyl-1H-indol-1-yl)methyl]benzyl}amino)phenyl]propanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 3-(4-{[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate (0.583 g, 1.60 mmol), {4-[(2-phenyl-1H-indol-1-yl)methyl]phenyl}methanol (0.470 g, 1.50 mmol) and triphenylphosphine (0.787 g, 3.00 mmol) in tetrahydrofuran (25 mL) was stirred under ice-cooling, and diethyl azodicarboxylate (40% toluene solution, 1.36 mL, 3.00 mmol) was added. The mixture was allowed to warm to room temperature and stirred for 3 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 as a brown 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-9f404a8fd2324d27b198585005e73160
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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