Triphenylphosphine → Methyl 4-{[[(2,4-dinitrophenyl)sulfonyl]({1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}methyl)amino]methyl}benzoate

HRID 509302

Reaction equation

HRID 509302 reaction equation
[CH3:1][Si:2]([CH2:5][N:6]1[CH:10]=[C:9]([CH2:11]O)[N:8]=[N:7]1)([CH3:4])[CH3:3].[N+:13]([C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=1[S:25]([NH:28][CH2:29][C:30]1[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:32][CH:31]=1)(=[O:27])=[O:26])([O-:15])=[O:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>CCOC(C)=O.C1C=CC=CC=1>[N+:13]([C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=1[S:25]([N:28]([CH2:29][C:30]1[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:32][CH:31]=1)[CH2:11][C:9]1[N:8]=[N:7][N:6]([CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4])[CH:10]=1)(=[O:26])=[O:27])([O-:15])=[O:14]

Participants

7

Reactant 4

HCID 11776Triphenylphosphine2×HCID 5462977Diethyl azodicarboxylate2×HCID 59627317(1-((Trimethylsilyl)methyl)-1h-1,2,3-triazol-4-yl)methanolHCID 59627340Methyl 4-({[(2,4-dinitrophenyl)sulfonyl]amino}methyl)benzoate

Product 1

HCID 59627272Methyl 4-{[[(2,4-dinitrophenyl)sulfonyl]({1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}methyl)amino]methyl}benzoate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of {1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}methanol (241 mg, 1.30 mmol), methyl 4-({[(2,4-dinitrophenyl)sulfonyl]amino}methyl)benzoate (514 mg, 1.30 mmol), triphenylphosphine (409 mg, 1.56 mmol) and benzene (4.34 mL) was treated with diethylazodicarboxylate (247 uL, 1.56 mmol). After one hour additional portions of triphenylphosphine (204 mg, 0.780 mmol) and diethylazodicarboxylate (124 uL, 0.780 mmol) The reaction was diluted with EtOAc and washed with 2M aq. HCl 2×, water, brine, dried (MgSO4) and concentrated to afford a brown oil used crude in the next reaction. MS: cal'd 563 (MH+), exp 563 (MH+).

Workup

  1. washwashed with 2M aq. HCl 2×, water, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customto afford a brown oil
  5. customin the next reaction

Sources & evidence

ORD record
ord-fbd65a37cabb4723994529d43b4a7427
Source dataset
uspto-grants-2015_08
Patent number
US09096559B2

Linked notes

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