Triethylamine → HCID 59534044, compound

HRID 1697264Notes

Reaction equation

HRID 1697264 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1B(O)O.[Cl:14][C:15]1[CH:16]=[C:17]([S:22]([NH:25][CH2:26][P:27](=[O:44])([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)(=[O:24])=[O:23])[CH:18]=[C:19]([Cl:21])[CH:20]=1.C(N(CC)CC)C>O1CCCC1.[Cu].II.CC(O)=O>[Cl:14][C:15]1[CH:16]=[C:17]([S:22]([N:25]([CH2:26][P:27](=[O:44])([O:36][CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)(=[O:23])=[O:24])[CH:18]=[C:19]([Cl:21])[CH:20]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2734375(Naphthalen-2-yl)boronic acidHCID 59534005Dibenzyl[(3,5-dichloro-phenylsulphonylamino)-methyl]-phosphonate

Product 1

HCID 59534044HCID 59534044, compound

Reagents, catalysts & solvents 2

HCID 131711869copper II-acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

89 mg 2-naphthaleneboronic acid are added to a mixture of 130 mg dibenzyl [(3,5-dichloro-phenylsulphonylamino)-methyl]-phosphonate and 100 mg molecular sieve (4 Å) in 8 ml of tetrahydrofuran. Then 47 mg copper-II-acetate and 72 μl triethylamine are added and the reaction mixture is stirred for 24 hours at ambient temperature. For working up the reaction mixture is filtered. The filter cake is washed with tetrahydrofuran and the filtrate is evaporated down in vacuo. The flask residue is divided between concentrated aqueous ammonia solution and methylene chloride. The aqueous phase is extracted with methylene chloride and the combined organic phases are washed with 1 N sodium hydroxide solution, dried on magnesium sulphate and evaporated down. The crude product is purified by chromatography through a silica gel column.

Workup

  1. filtrationis filtered
  2. washThe filter cake is washed with tetrahydrofuran
  3. customthe filtrate is evaporated down in vacuo
  4. extractionThe aqueous phase is extracted with methylene chloride
  5. washthe combined organic phases are washed with 1 N sodium hydroxide solution
  6. customdried on magnesium sulphate
  7. customevaporated down
  8. customThe crude product is purified by chromatography through a silica gel column

Sources & evidence

ORD record
ord-4ed4bcad16bd43b3a42eaf5d1bad426d
Source dataset
uspto-grants-2012_04
Patent number
US08163911B2

Reaction notes

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