Triethylamine → HCID 70419999, compound

HRID 649243Notes

Reaction equation

HRID 649243 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl.[CH3:14][O:15][C:16](=[O:19])[CH2:17][NH2:18].C(N(CC)CC)C.[CH2:27]([P:34](Cl)([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:35])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.P([O-])(OCC1C=CC=CC=1)OCC1C=CC=CC=1.S(Cl)(Cl)(=O)=O>C(Cl)(Cl)Cl>[CH2:36]([P:34]([NH:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:35])[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1.[CH3:14][O:15][C:16](=[O:19])[CH2:17][NH2:18]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 24648Sulfuryl chlorideHCID 12809684Dibenzylphosphinic chlorideHCID 21904359DibenzylphosphiteHCID 70420509HCID 70420509, compound

Product 1

HCID 70419999HCID 70419999, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

2 g of L-phenylalanine-glycine methyl ester hydrochloride (7.4 mmoles) are put in suspension in 20 ml of anhydrous chloroform. 1.50 g of triethylamine (15 mmoles) are added. The solid enters into solution. The solution is cooled to 0° C. and 2.17 g (7.4 mmoles) of dibenzyl phosphoryl chloride freshly prepared from dibenzyl phosphite and sulfuryl chloride are added while stirring for 30 minutes. The mixture is allowed to stand for 20 hours at room temperature. The precipitate formed is filtered and the filtrate is washed in succession with 30 ml of 1N HCl, 20 ml of water, 20 ml of 10% bicarbonate, then 2×30 ml of water. The organic solution is dried on anhydrous Na2SO4 and evaporated under a vacuum. A pale yellow solid is obtained which is recrystallized in ethyl acetate.

Workup

  1. additionare added
  2. waitto stand for 20 hours at room temperature
  3. customThe precipitate formed
  4. filtrationis filtered
  5. washthe filtrate is washed in succession with 30 ml of 1N HCl, 20 ml of water, 20 ml of 10% bicarbonate
  6. dry with materialThe organic solution is dried on anhydrous Na2SO4
  7. customevaporated under a vacuum
  8. customA pale yellow solid is obtained which
  9. customis recrystallized in ethyl acetate

Sources & evidence

ORD record
ord-d57968be17c94004a1cce1ebea2dbe29
Source dataset
uspto-grants-1988_04
Patent number
US04738803

Reaction notes

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