Triethylamine → HCID 53672487, compound

HRID 328086Notes

Reaction equation

HRID 328086 reaction equation
Cl.[NH2:2][C@H:3]([C:5]([NH:7][CH2:8][P:9](=[O:14])([O:12][CH3:13])[O:10][CH3:11])=[O:6])[CH3:4].[CH2:15]([O:22][C:23]([NH:25][C@H:26]([C:28](O)=[O:29])[CH3:27])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>CN(C)C=O>[CH2:15]([O:22][C:23]([NH:25][C@H:26]([C:28]([NH:2][C@H:3]([C:5]([NH:7][CH2:8][P:9](=[O:14])([O:10][CH3:11])[O:12][CH3:13])=[O:6])[CH3:4])=[O:29])[CH3:27])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 736104N-carbobenzyloxyalanineHCID 86734611HCID 86734611, compound

Product 1

HCID 53672487HCID 53672487, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

24.65 g of dimethyl (L-alanylamino)-methylphosphonate hydrochloride and 32.0 g of the N-hydroxysuccinimide ester of N-benzyloxycarbonyl-L-alanine were stirred in 200 ml of dry dimethylformamide while 14 ml of dry triethylamine were added dropwise at 20° C. The mixture was stirred overnight and then the triethylamine hydrochloride filtered off and washed with a small amount of dimethylformamide. The filtrate was evaporated under an oil-pump vacuum, the residue treated with 150 ml of water and then extracted with four 125 ml portions of chloroform. The combined chloroform layers were washed with a 20 % potassium carbonate solution, separated and dried over sodium sulphate. The sodium sulphate was filtered off, the filtrate evaporated firstly under a water-pump vacuum and then under an oil-pump vacuum and the residue taken up in 100 ml of ethyl acetate. About 100 ml of ether were added to faint turbidity when crystallization began. After refrigeration overnight, the solid was filtered off, washed successively with ethyl acetate/ether (1:1) and ether and then dried in vacuo. Recrystallization from 200 ml of boiling ethyl acetate by the addition of 200 ml of ether gave 27.8 g of dimethyl [(N-benzyloxycarbonyl-L-alanyl-L-alanyl)amino] -methylphosphonate of melting point 106°-108° C; [α]D20 =- 37.4° (c =1% in glacial acetic acid).

Workup

  1. additionwere added dropwise at 20° C
  2. filtrationthe triethylamine hydrochloride filtered off
  3. washwashed with a small amount of dimethylformamide
  4. customThe filtrate was evaporated under an oil-pump vacuum
  5. additionthe residue treated with 150 ml of water
  6. extractionextracted with four 125 ml portions of chloroform
  7. washThe combined chloroform layers were washed with a 20 % potassium carbonate solution
  8. customseparated
  9. dry with materialdried over sodium sulphate
  10. filtrationThe sodium sulphate was filtered off
  11. customthe filtrate evaporated firstly under a water-pump vacuum
  12. additionAbout 100 ml of ether were added to faint turbidity when crystallization
  13. waitAfter refrigeration overnight
  14. filtrationthe solid was filtered off
  15. washwashed successively with ethyl acetate/ether (1:1) and ether
  16. customdried in vacuo
  17. customRecrystallization from 200 ml of boiling ethyl acetate
  18. additionby the addition of 200 ml of ether

Sources & evidence

ORD record
ord-1b9237296c6d4668911a0f6c6bfb0ca3
Source dataset
uspto-grants-1977_04
Patent number
US04016148

Reaction notes

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