Zinc acetate (USP) → HCID 136341386, compound

HRID 1502932Notes

Reaction equation

HRID 1502932 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]([C:15]2[C:16]3[NH:20][C:19]([C:21]([C:67]4[CH:72]=[CH:71][CH:70]=[C:69]([O:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][Br:80])[CH:68]=4)=[C:22]4[N:66]=[C:25]([C:26]([C:52]5[CH:57]=[CH:56][CH:55]=[C:54]([O:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][Br:65])[CH:53]=5)=[C:27]5[NH:51][C:30](=[C:31]([C:37]6[CH:42]=[CH:41][CH:40]=[C:39]([O:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][Br:50])[CH:38]=6)[C:32]6[CH:33]=[CH:34][C:35]=2[N:36]=6)[CH:29]=[CH:28]5)[CH:24]=[CH:23]4)=[CH:18][CH:17]=3)[CH:12]=[CH:13][CH:14]=1.O.O.C([O-])(=O)C.[Zn+2:87].C([O-])(=O)C>C(Cl)(Cl)Cl.CO>[Zn+2:87].[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]([C:15]2[C:16]3[NH:20][C:19]([C:21]([C:67]4[CH:72]=[CH:71][CH:70]=[C:69]([O:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][Br:80])[CH:68]=4)=[C:22]4[N:66]=[C:25]([C:26]([C:52]5[CH:57]=[CH:56][CH:55]=[C:54]([O:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][Br:65])[CH:53]=5)=[C:27]5[NH:51][C:30](=[C:31]([C:37]6[CH:42]=[CH:41][CH:40]=[C:39]([O:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][Br:50])[CH:38]=6)[C:32]6[CH:33]=[CH:34][C:35]=2[N:36]=6)[CH:29]=[CH:28]5)[CH:24]=[CH:23]4)=[CH:18][CH:17]=3)[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 2724192Zinc acetate (USP)HCID 136341387HCID 136341387, compound

Product 1

HCID 136341386HCID 136341386, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

A porphyrin 5a (266 mg, 0.200 mmol) was dissolved in anhydrous chloroform, and the mixture was stirred at 70° C. for 45 min under a nitrogen atmosphere. To the mixture was added zinc acetate dihydrate (439 mg, 2.00 mmol) dissolved in anhydrous methanol (4 mL), and the mixture was stirred at 70° C. for 4 hours. The mixture was cooled to room temperature, concentrated and then washed with water. The mixture was dried over sodium sulfate and concentrated. The residual material was purified by silica gel column chromatography [methylene chloride/hexane (2:1)], to give compound 6a (purple-red solid) (yield: 272 mg, 98%).

Workup

  1. stirringthe mixture was stirred at 70° C. for 4 hours
  2. temperatureThe mixture was cooled to room temperature
  3. concentrationconcentrated
  4. washwashed with water
  5. dry with materialThe mixture was dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residual material was purified by silica gel column chromatography [methylene chloride/hexane (2:1)]

Sources & evidence

ORD record
ord-f7a1d89d37354d53b46d3683077b7e55
Source dataset
uspto-grants-2015_12
Patent number
US09211534B2

Reaction notes

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