Potassium Hydroxide → HCID 86591118, compound

HRID 858276Notes

Reaction equation

HRID 858276 reaction equation
[CH3:1][C:2]1([CH3:35])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]3[CH:19]=[C:18]([C:20]4[CH:25]=[CH:24][C:23]([C:26](O)=[O:27])=[CH:22][CH:21]=4)[CH:17]=[CH:16][C:15]=3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:5]=[CH:4][C:3]1=2.[OH-].[K+].C[Si](C)(C)[O:40][NH2:41].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>O.ClCCl.C(O)C>[CH3:1][C:2]1([CH3:35])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]3[CH:19]=[C:18]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([NH:41][OH:40])=[O:27])=[CH:22][CH:21]=4)[CH:17]=[CH:16][C:15]=3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:5]=[CH:4][C:3]1=2

Participants

8

Reactant 5

HCID 14797Potassium HydroxideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2734666O-(Trimethylsilyl)hydroxylamineHCID 10139495HCID 10139495, compound

Product 1

HCID 86591118HCID 86591118, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21908982Water methylene chlorideSolvent

Procedure

2.00 g (4.3 mmol) of the acid obtained in Example 14, 30 ml of ethanol and 290 mg (5.2 mmol) of powdered potassium hydroxide are successively introduced into a three-necked flask under a stream of nitrogen. The reaction medium is stirred for thirty minutes at room temperature and is then evaporated to dryness. The residue is taken up in 80 ml of dichloromethane and 673 mg (4.8 mmol) of O-(trimethylsilyl)hydroxylamine and 645 mg (4.8 mmol) of 1-hydroxybenzotriazole (HOBT) are added. After cooling the reaction medium to 0° C., 915 mg (4.8 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) are added and the solution obtained is stirred for one hour at 0° C. and then for sixteen hours at room temperature. The reaction medium is poured into a water/dichloromethane mixture and extracted with dichloromethane, and the organic phase is washed with water to neutral pH, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture composed of 20% ethyl acetate and 80% heptane. After evaporation of the solvents, 530 mg (22%) of the expected product are collected in the form of a beige-coloured solid with a melting point of 105–108° C.

Workup

  1. customis then evaporated to dryness
  2. temperatureAfter cooling the reaction medium to 0° C.
  3. customthe solution obtained
  4. stirringis stirred for one hour at 0° C.
  5. waitfor sixteen hours at room temperature
  6. extractionextracted with dichloromethane
  7. washthe organic phase is washed with water to neutral pH
  8. dry with materialdried over magnesium sulphate
  9. customevaporated
  10. customThe residue obtained
  11. customis purified by chromatography on a column of silica
  12. washeluted with a mixture
  13. customAfter evaporation of the solvents, 530 mg (22%) of the expected product
  14. customare collected in the form of a beige-coloured solid with a melting point of 105–108° C.

Sources & evidence

ORD record
ord-b17fb54b088643a79b0da3cca265b275
Source dataset
uspto-grants-2006_12
Patent number
US07148245B2

Reaction notes

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