Triphenylphosphine → HCID 178499916, compound

HRID 508041Notes

Reaction equation

HRID 508041 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]=[C:34](/[CH:37]=[N:38]/[C:39]3[CH:44]=[CH:43][C:42]([CH2:45]O)=[CH:41][CH:40]=3)[S:35][CH:36]=2)[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]([CH2:45][C:42]1[CH:41]=[CH:40][C:39](/[N:38]=[CH:37]/[C:34]2[S:35][CH:36]=[C:32]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:33]=2)=[CH:44][CH:43]=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 23157467Methyl 3-(4-{[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoateHCID 178519697HCID 178519697, compound

Product 1

HCID 178499916HCID 178499916, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(4-{[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate (364 mg, 1.0 mmol), (4-{[(1E)-(4-phenyl-1,3-thiazol-2-yl)methylene]amino}phenyl)methanol (297 mg, 1.0 mmol) and triphenylphosphine (393 mg, 1.5 mmol) in tetrahydrofuran (4 mL) was added diethyl azodicarboxylate (40% toluene solution, 660 mg, 1.5 mmol) at room temperature, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was purified by silica gel column chromatography (5%-70% ethyl acetate/hexane) to give a yellow oil containing the title compound.

Workup

  1. customThe reaction mixture was purified by silica gel column chromatography (5%-70% ethyl acetate/hexane)
  2. customto give a yellow oil

Sources & evidence

ORD record
ord-095d44eed5664a7387c1f00c651ba319
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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