Triethylamine → HCID 12837864, compound

HRID 1065297Notes

Reaction equation

HRID 1065297 reaction equation
[C:1]([NH:4][C:5](=[O:8])[CH2:6][SH:7])(=[O:3])[CH3:2].[C:9]([CH2:13][CH2:14][C:15](Cl)=[O:16])([O:11][CH3:12])=[O:10].C(N(CC)CC)C>ClCCl>[C:1]([NH:4][C:5](=[O:8])[CH2:6][S:7][C:15](=[O:16])[CH2:14][CH2:13][C:9]([O:11][CH3:12])=[O:10])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 12837860HCID 12837860, compound

Product 1

HCID 12837864HCID 12837864, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The concentrated product of Step A. above was added to 100 ml. of dichloromethane and cooled to -5° C. under nitrogen. There was then added 8.3 g. (0.055 mole) of 3-carbomethoxypropionyl chloride in 20 ml. of dichloromethane, over from 5 to 10 minutes. Next, there was added 5.57 g. (0.055 mole) of triethylamine in 20 ml. of dichloromethance and the reaction mixture was aged for 1 hour at -5° C., then permitted to come to room temperature over 2 hours. The reaction mixture was then concentrated under vacuum after having been made slightly acidic with acetic acid. Ice water was then added to the reaction mixture, and the water was extracted with dichloromethane dried over magnesium sulfate and concentrated to an oil of 15.4 g. The oil was changed to a silica gel column and eluted with 25% ethylacetate/hexane to obtain 2.3 g. of final product having an m.p. of 111°-113° C.

Workup

  1. additionabove was added to 100 ml
  2. additionThere was then added 8.3 g
  3. customover from 5 to 10 minutes
  4. additionNext, there was added 5.57 g
  5. waitto come to room temperature over 2 hours
  6. concentrationThe reaction mixture was then concentrated under vacuum
  7. additionIce water was then added to the reaction mixture
  8. extractionthe water was extracted with dichloromethane
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated to an oil of 15.4 g
  11. washeluted with 25% ethylacetate/hexane
  12. customto obtain 2.3 g

Sources & evidence

ORD record
ord-b217c95d750940839f009f809da28028
Source dataset
uspto-grants-1982_05
Patent number
US04329363

Reaction notes

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