Dichloromethane → 2,3,4,5,6-Pentafluorophenyl 4-({3-[bis(4-methoxyphenyl)phenylmethoxy]propyl}{4-[(2-chloro-4-nitrophenyl)diazenyl]phenyl}amino)butanoate

HRID 599381Notes

Reaction equation

HRID 599381 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:45]2[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][CH:46]=2)([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[O:10][CH2:11][CH2:12][CH2:13][N:14]([C:21]2[CH:26]=[CH:25][C:24]([N:27]=[N:28][C:29]3[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][C:30]=3[Cl:38])=[CH:23][CH:22]=2)[CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:5][CH:4]=1.C(N(CC)CC)C.C(Cl)Cl.FC(F)(F)C(O[C:68]1[C:73]([F:74])=[C:72]([F:75])[C:71]([F:76])=[C:70]([F:77])[C:69]=1[F:78])=O>CCCCCC.C(OCC)(=O)C>[CH3:52][O:51][C:48]1[CH:49]=[CH:50][C:45]([C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[O:10][CH2:11][CH2:12][CH2:13][N:14]([C:21]2[CH:26]=[CH:25][C:24]([N:27]=[N:28][C:29]3[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][C:30]=3[Cl:38])=[CH:23][CH:22]=2)[CH2:15][CH2:16][CH2:17][C:18]([O:20][C:68]2[C:69]([F:78])=[C:70]([F:77])[C:71]([F:76])=[C:72]([F:75])[C:73]=2[F:74])=[O:19])=[CH:46][CH:47]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 4327891Pentafluorophenyl TrifluoroacetateHCID 865847214-({3-[Bis(4-methoxyphenyl)phenylmethoxy]propyl}-(4-[(2-chloro-4-nitrophenyl)diazenyl]phenyl}amino)butanoic acid

Product 1

HCID 865847202,3,4,5,6-Pentafluorophenyl 4-({3-[bis(4-methoxyphenyl)phenylmethoxy]propyl}{4-[(2-chloro-4-nitrophenyl)diazenyl]phenyl}amino)butanoateYield 41%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

To the flask containing 21 (10 mmol) is added 7 mL of triethylamine followed by 100 mL of methylene chloride, 2.05 mL of pentafluorophenyl trifluoroacetate (PFP-TFA) is then added. The solution is stirred for half an hour. At the end of this time, the reaction is usually complete. (TLC: 2:1 hexane/ethyl acetate). The solvent is removed on the rotary evaporator to give a syrup which is chromatographed on silica eluting with 1:3 ethyl acetate/hexane. Appropriate fractions are collected, combined, evaporated and dried under vacuum. The yield is 41%. 1H NMR (DMSO-d6) δ 8.43 (d, J=2.5 Hz, aromatic proton, 1H), 8.24 (dd, J1=9 Hz, J2=2.5 Hz, aromatic proton, 1H), 7.83 (d, J=9 Hz, aromatic proton, 1H), 7.78 (d, J=9 Hz, aromatic proton, 1H), 7.42-7.15 (m, aromatic protons, 10H), 7.07 (m, aromatic protons, 2H), 7.00-6.80 (m, aromatic protons, 4H), 3.72 (s, 2×CH3, 6H), 3.56 (m, aliphatic protons, 2H), 3.48 (t, J=6.3 Hz, aliphatic protons, 2H), 3.08 (t, J=5 Hz, aliphatic protons, 2H), 2.89 (t, J=7 Hz, aliphatic protons, 2H), 1.95 (m, aliphatic protons, 2H), 1.86 (m, aliphatic protons, 2H).

Workup

  1. additionis then added
  2. customThe solvent is removed on the rotary evaporator
  3. customto give a syrup which
  4. customis chromatographed on silica eluting with 1:3 ethyl acetate/hexane
  5. customAppropriate fractions are collected
  6. customevaporated
  7. customdried under vacuum

Sources & evidence

ORD record
ord-af1d4eacd7d44a559df0e0b575d37c51
Source dataset
uspto-grants-2011_03
Patent number
US07897736B2

Reaction notes

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