HCID 135399599, compound → HCID 137252520, compound

HRID 1920887Notes

Reaction equation

HRID 1920887 reaction equation
[CH2:1]([C:4]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:18]3[NH:22][C:21]([C:23]([C:55]4[CH:60]=[CH:59][C:58]([CH3:61])=[CH:57][CH:56]=4)=[C:24]4[N:54]=[C:27]([C:28]([C:47]5[CH:52]=[CH:51][C:50]([CH3:53])=[CH:49][CH:48]=5)=[C:29]5[NH:46][C:32](=[C:33]([C:39]6[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=6)[C:34]6[CH:35]=[CH:36][C:37]=2[N:38]=6)[CH:31]=[CH:30]5)[CH:26]=[CH:25]4)=[CH:20][CH:19]=3)=[CH:13][CH:12]=1)([CH2:8][CH:9]=[CH2:10])[CH2:5][CH:6]=[CH2:7])[CH:2]=[CH2:3].[Zn:62](OC(C)=O)OC(C)=O.O.O>C(Cl)(Cl)Cl.CO>[Zn+2:62].[CH2:1]([C:4]([C:11]1[CH:12]=[CH:13][C:14]([C:17]2[C:18]3[NH:22][C:21]([C:23]([C:55]4[CH:56]=[CH:57][C:58]([CH3:61])=[CH:59][CH:60]=4)=[C:24]4[N:54]=[C:27]([C:28]([C:47]5[CH:52]=[CH:51][C:50]([CH3:53])=[CH:49][CH:48]=5)=[C:29]5[NH:46][C:32](=[C:33]([C:39]6[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=6)[C:34]6[CH:35]=[CH:36][C:37]=2[N:38]=6)[CH:31]=[CH:30]5)[CH:26]=[CH:25]4)=[CH:20][CH:19]=3)=[CH:15][CH:16]=1)([CH2:8][CH:9]=[CH2:10])[CH2:5][CH:6]=[CH2:7])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 135399599HCID 135399599, compoundHCID 178476752HCID 178476752, compound

Product 1

HCID 137252520HCID 137252520, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

A solution of 1 (132 mg, 167 μmol) in CHCl3 (13 mL) was treated with a solution of Zn(OAc)2.2H2O (183 mg, 0.832 mmol) in MeOH (2.6 mL) at room temperature. The reaction was followed by TLC. The reaction was complete in 2 h. The reaction mixture was washed with saturated aqueous NH4Cl and extracted with CH2Cl2. The combined organic layer was dried (Na2SO4), concentrated and chromatographed [silica, hexanes/ethyl acetate (9:1)] to afford a pink solid (132 mg, 93%): 1H NMR δ 2.66-2.78 (m, 15H), 5.12-5.28 (m, 6H), 5.80-5.96 (m, 3H), 7.50-7.60 (m, 6H), 7.67 (d, J=8.4 Hz, 2H), 8.04-8.14 (m, 6H), 8.16 (d, J=8.4 Hz, 2H), 8.88-8.94 (m, 2H), 8.94-9.02 (m, 6H); MALDI-MS obsd 852.4; FABMS obsd 852.3193, calcd 852.3170 (C57H48N4Zn); λabs 424, 551 nm.

Workup

  1. washThe reaction mixture was washed with saturated aqueous NH4Cl
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customchromatographed [silica, hexanes/ethyl acetate (9:1)]

Sources & evidence

ORD record
ord-c32643fbf9b64db989dbb797f7ccee30
Source dataset
uspto-grants-2012_05
Patent number
US08173630B2

Reaction notes

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