Triethylamine → HCID 54290744, compound

HRID 328082Notes

Reaction equation

HRID 328082 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([OH:16])=O)[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:18][CH2:19][P:20](=[O:25])([O:23][CH3:24])[O:21][CH3:22].C(N(CC)CC)C>CN(C)C=O>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([NH:18][CH2:19][P:20](=[O:25])([O:23][CH3:24])[O:21][CH3:22])=[O:16])[CH3:13])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 736104N-carbobenzyloxyalanineHCID 13310505HCID 13310505, compound

Product 1

HCID 54290744HCID 54290744, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9.6 g (0.03 mol) of the N-hydroxysuccinimide ester of N-benzyloxycarbonyl-L-alanine and 5.26 g (0.03 mol) of dimethyl aminomethylphosphonate hydrochloride were stirred in 65 ml of dry dimethylformamide. While stirring and maintaining the temperature below 20° C, there were added dropwise 4.2 ml of dry triethylamine. The mixture was then stirred overnight at room temperature. The triethylamine hydrochloride was filtered off and washed with a little dimethylformamide. The filtrate was evaporated under an oil-pump vacuum and at a bath temperature below 40° C. The residual oil was treated with 40 ml of water and the resulting mixture extracted with four 40 ml portions of chloroform. The combined organic phases were washed with a small volume of a strong potassium carbonate solution and then dried over sodium sulphate. The sodium sulphate was filtered off and the filtrate evaporated first under a water-pump vacuum and then under an oil-pump vacuum. There were obtained 11.0 g of dimethyl [(N-benzyloxycarbonyl-L-alanyl)amino]-methylphosphonate as an oil with the expected N.M.R. spectrum.

Workup

  1. temperaturemaintaining the temperature below 20° C, there
  2. stirringThe mixture was then stirred overnight at room temperature
  3. filtrationThe triethylamine hydrochloride was filtered off
  4. washwashed with a little dimethylformamide
  5. customThe filtrate was evaporated under an oil-pump vacuum and at a bath temperature below 40° C
  6. additionThe residual oil was treated with 40 ml of water
  7. extractionthe resulting mixture extracted with four 40 ml portions of chloroform
  8. washThe combined organic phases were washed with a small volume of a strong potassium carbonate solution
  9. dry with materialdried over sodium sulphate
  10. filtrationThe sodium sulphate was filtered off
  11. customthe filtrate evaporated first under a water-pump vacuum

Sources & evidence

ORD record
ord-977ce0540b2a4ccfb49684cd13a8de61
Source dataset
uspto-grants-1977_04
Patent number
US04016148

Reaction notes

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